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UChicago Supplemental Essays 2024-25 – Prompts and Advice

July 8, 2024

UChicago has long been known for its “provocative” essay prompts, viewing them as a chance for “students to talk about themselves, their tastes, and their ambitions.” The University of Chicago admissions committee invites you to approach the UChicago supplemental essays with “utter seriousness, complete fancy, or something in between.” While writing this “uncommon essay” sounds like a real lark, we have to keep in mind the sobering facts that UChicago admits just 4% of applicants, and the mid-50% SAT range of those who enroll is 1510-1560. This level of competition places the UChicago essay prompts squarely in the spotlight.

(Want to learn more about How to Get Into UChicago? Visit our blog entitled:  How to Get Into the University of Chicago: Admissions Data and Strategies  for all of the most recent admissions data as well as tips for gaining acceptance.)

When applying to an institution like the University of Chicago that rejects 19 of every 20 applicants, you’ll need to put maximum effort into every area of the application, including the two UChicago supplemental essays. Below are UChicago’s supplemental prompts for the 2024-25 admissions cycle along with our advice for composing a winning essay.

UChicago Essay Prompts – Question 1  (Required)

How does the University of Chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future? Please address with some specificity your own wishes and how they relate to UChicago.

For the absurd level of uniqueness in the prompt choices in Question #2, Question #1 is as common as they come—the good ol’ “Why Us?” essay, Chicago style!

How to write a winning “Why University of Chicago?” essay

• Specify how you will take advantage of UChicago’s endless resources, both inside and outside of the classroom.
• Cite specific academic programs, professors, research opportunities, internship/externship programs, study abroad programs, student-run organizations, etc.
• Show evidence of how your past/current endeavors will carry over onto the University’s campus community.
• Lastly, note any special talents and passions that you bring to the University of Chicago.

Examples of items to include in a “Why UChicago?” essay

Examples of items that quality “Why UChicago?” essays may touch upon include:

• Two-thirds of UChicago professors live in Hyde Park, making for a particularly cohesive campus.
• 80% of undergrads elect to participate in undergraduate research .
• Additionally, the quarter system allows students to explore a greater number of courses each year in a more in-depth manner.
• 85% of UChicago classes enroll fewer than 25 students.
• The school has 160+ research centers, institutes, and committees.

UChicago Supplemental Essays (Continued)

• Many students win Rhodes, Marshall, and Fulbright Scholarships after graduation.
• The Jeff Metcalf Internship Program also offers 3,500 paid internships.
• UChicago has 450 student organizations .
• The university sponsors 66 study abroad programs in 31 cities ; many include chances to study with UChicago professors around the globe.

Of course, these are just a small sampling of the thousands of possible features that could be part of a successful essay, but we hope this helps your brainstorming session take flight!

Question 2: Extended Essay (Required; Choose one)

Before offering a few words about how one might address each of the following prompts, we want to stress to future UChicago applicants that there is no right way to talk about color-infused expressions, demoted planets, or Fermi estimation problems. What matters is that your response to any of the following prompts demonstrates your excellence and creativity as a writer. If the first five prompts don’t appeal to you, there is no downside in constructing your own via option #6.

University of Chicago Supplemental Essays

Essay option 1.

We’re all familiar with green-eyed envy or feeling blue, but what about being “caught purple-handed”? Or “tickled orange”? Give an old color-infused expression a new hue and tell us what it represents.

An applicant can quite easily take this in a very serious or seriously humorous direction. Our only suggestion is that your rule doesn’t include the phrase, “If it’s yellow, let it mellow.” Or, it can. This is the UChicago supplemental section. Anything goes. Get weird.

Essay Option 2

“Ah, but I was so much older then / I’m younger than that now” – Bob Dylan. In what ways do we become younger as we get older?

As with all UChicago questions, you can take this in a serious or off-the-wall direction. For example, as we get older, many of us need additional physical and/or mental support, similar to young children. Alternatively, we may adopt a “younger” attitude as we get older, perhaps not caring as much about what others think about us, or vowing to live life more spontaneously. Or, you could get a little wild and talk about how the version of yourself in any given photograph will seem younger and younger the older you get. Overall, if ruminating on Bob Dylan lyrics appeals to you, knock yourself out. If not, keep moving down the list of prompts…

Essay Option 3

Pluto, the demoted planet. Ophiuchus, the thirteenth Zodiac. Andy Murray, the fourth to tennis’s Big Three. Every grouping has something that doesn’t quite fit in. Tell us about a group and its unofficial member, why (or why not) should it be excluded?

A few years back, UChicago offered a prompt for imagining that the moon was made of cheese or Neptune from soap. To that prompt, we advised that it didn’t matter if you wrote about a quasar made of Jergens Enriching Shea Butter or Jupiter’s moons constructed from Bored Ape NFTs—your imagination and writing ability are what matters here. The latter half of that advice remains applicable to this prompt. There are an endless number of interesting groups that may be worth unpacking, so if you happen to have one in mind, go wild. The explanation will be far more important than the group itself.

Essay Option 4

“Daddy-o”, “Far Out”, “Gnarly”: the list of slang terms goes on and on. Sadly, most of these aren’t so “fly” anymore – “as if!” Name an outdated slang from any decade or language that you’d bring back and explain why you totally “dig it.”

If you, as a ridiculously busy applicant, have time to spare, this is a pretty fun prompt to ponder. The only downside is that—since this is so specific— you may not be able to reuse your composition for any other college to which you are applying. That said, if you’ve always felt called to muse about the near-constant use of “Booyah” in the ’90s or reflect on a Spanish slang word from the 70s that your grandmother still says on a regular basis, your day has come.

Essay Option 5

How many piano tuners are there in Chicago? What is the total length of chalk used by UChicago professors in a year? How many pages of books are in the Regenstein Library? These questions are among a class of estimation problems named after University of Chicago physicist Enrico Fermi. Create your own Fermi estimation problem, give it your best answer, and show us how you got there.

This essay affords applicants a chance to flex their intellectual muscles and show off a talent for navigating complex answers. As illustrated in the built-in examples, the estimation problems may be straightforward (number of book pages in a library) or zany (total length of chalk used in a year). Your explanation of how you arrived at your answer is where the real creativity comes in.

Essay Option 6

And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the University of Chicago; take a little risk, and have fun!

If you elect to go with an archived prompt, you can locate some past entries around the internet such as here and here . There are also a number of past prompts listed directly on the UChicago admissions website . A good number of applicants we have worked with avail themselves of the flexibility offered by this restriction-free offering.

How important are the UChicago essay prompts?

The University of Chicago lists six factors as being “very important” to the admissions committee and the essays are among them. In addition to the essays, UChicago most heavily weighs the rigor of your secondary school record, recommendations, extracurricular activities, talent/ability, and character/personal qualities. Clearly, the Common App and supplemental essays are among the most important considerations for the University of Chicago in its decision-making process.

UChicago Supplemental Essays – Personalized Assistance

Lastly, if you are interested in working with one of College Transitions’ experienced and knowledgeable essay coaches as you craft your UChicago supplemental essays, we encourage you to get a quote  today.

Ready to start working on your essays? You might consider checking out the following:

• Common App Essay Prompts
• 10 Instructive Common App Essay Examples
• College Application Essay Topics to Avoid
• How to Brainstorm a College Essay
• 25 Inspiring College Essay Topics
• “Why This College?” Essay Examples
• How to Write the Community Essay
• College Essay

Dave Bergman

Dave has over a decade of professional experience that includes work as a teacher, high school administrator, college professor, and independent educational consultant. He is a co-author of the books The Enlightened College Applicant (Rowman & Littlefield, 2016) and Colleges Worth Your Money (Rowman & Littlefield, 2020).

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University of Chicago 2024-25 Supplemental Essay Prompt Guide

Early Action/Decision: Nov 1

Regular Decision Deadline: Jan 2

University of Chicago 2024-25 Application Essay Question Explanations

The Requirements: 2 essays of 1-2 pages each

Supplemental Essay Type(s): Why , Oddball

How to Write The UChicago Essays

This is it, the infamous UChicago supplemental application. These quirky prompts have been a rite of passage for generations of applicants, so before you dive in, just remember: if they could do it, so can you! Your goal in writing your UChicago extended essay should be the same as ever: to reveal something new to admissions. It might even help to have a few ideas in mind before reading through your options. These prompts are so specific and strange that, in the end, the key is just to follow your instincts. What speaks to you right away? What inspires you?

UChicago Prompt Breakdowns

Question 1 ( required ), how does the university of chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future please address with some specificity your own wishes and how they relate to uchicago..

Think of this run-of-the-mill Why Essay as the overture to your magnum opus (i.e. the Extended Essay). Chicago wants you to cover all the bases—“learning, community, and future”—so as with any Why Essay, you’d best buckle down and do your homework. The more specific details you can incorporate into your essay, the more sincere and personal it will feel (and be!). Explore both academic and extracurricular opportunities. How will you pursue your interest in oceanography? With a major in Biology and a semester in Australia? What research opportunities will you pursue? Will joining the Club Crew team help you feel more connected to aquatic life despite your midwest location? One thing you won’t find on the school website, though, is that third piece, that “future” thing. Think about where you’d like to be five or ten years from now—your career or the impact you’d like to have or even just a geographic location. How will a UChicago education help you get there? How will your scholarly and social pursuits help you grow? Show admissions how UChicago is the bridge between the person you are and the person you hope to be.

Question 2: Extended Essay ( Required; Choose one )

Essay option 1, we’re all familiar with green-eyed envy or feeling blue, but what about being “caught purple-handed” or “tickled orange” give an old color-infused expression a new hue and tell us what it represents., – inspired by ramsey bottorff, class of 2026.

This is a great question for artists, those of you with synesthesia, or anyone who’s been down the rabbit hole of seasonal color theory on social media. If you have strong associations with different colors or are language-obsessed, then this is a great chance to combine logical and creative thinking to breathe new life into these old sayings. Look at a rainbow or color wheel and see if any feelings or ideas jump out to you. Maybe you feel a certain calm when you see fuchsia, so “out of the fuchsia” might mean a solution that came from deep meditation, a practice introduced to you by your late grandfather. Perhaps you associate sky blue with familial love, and “a blue thumb” would mean someone who is very in tune with their family, culture, and traditions. Ultimately, your argument will (hopefully) show admissions how your brain works and pepper in a few insights as to the kinds of things you hold dear along the way.

Essay Option 2

“ah, but i was so much older then / i’m younger than that now” – bob dylan. in what ways do we become younger as we get older, – inspired by joshua harris, class of 2016.

This prompt will surely appeal to the philosophers among you, as it invites you to consider the trajectory of a person’s lifetime. With such a broad field to choose from, your answers can vary from the biological (some of our blood cells regenerate every four months , so they are always younger than the rest of us) to the comedic ( embracing cartoons that you used to pretend you were too old for ) to the profound (dementia patients reverting to childhood). As you brainstorm, make a list of all possible examples of this phenomenon and choose the ones that get you excited and that you can weave together into an essay that reveals what matters to you. Remember, admissions wants to see both creative thinking and strong analytical capabilities while learning what makes you tick. If anyone else could put their name at the top of your essay, you haven’t identified the right topic yet.

Essay Option 3

Pluto, the demoted planet. ophiuchus, the thirteenth zodiac. andy murray, the fourth to tennis’s big three. every grouping has something that doesn’t quite fit in. tell us about a group and its unofficial member, why (or why not) should it be excluded, – inspired by veronica chang, class of 2022.

If you love finding patterns, solving puzzles, or identifying what holds groups together, this is the prompt for you! As you go through your daily life, start observing and jotting down instances of “the odd man out.” As your list increases, see which ones jump out to you. Maybe you have the perfect explanation for why Washington, DC can’t become a state. Perhaps you’re ready to defend the tomato’s inclusion as a vegetable even though it’s technically a fruit. As with the other prompts, your choice can be as serious or frivolous as you like, as long as it is well reasoned and creative! 

Essay Option 4

“daddy-o”, “far out”, “gnarly”: the list of slang terms goes on and on. sadly, most of these aren’t so “fly” anymore – “as if” name an outdated slang from any decade or language that you’d bring back and explain why you totally “dig it.”, – inspired by napat sakdibhornssup, class of 2028.

As language nerds, we at CEA love this prompt, which is perfect for pop culture buffs, linguistics fans, or those of you whose parents think their generation’s slang is “da bomb!” You can approach this either by choosing an old slang term you like and expounding upon it or by identifying gaps in our current English language use and finding a term to fit; what ideas or emotions are we leaving unexpressed without some crucial piece of missing slang? Sure, we can say something is “all that,” but do we need to indicate it’s “all that and a bag of chips ”? Maybe! Note that the prompt also allows you to choose slang from other languages, so those of you with multicultural backgrounds can highlight that through your choice of phrase. Bonus points if you weave in multiple examples as the prompt does so effortlessly!

Essay Option 5

How many piano tuners are there in chicago what is the total length of chalk used by uchicago professors in a year how many pages of books are in the regenstein library these questions are among a class of estimation problems named after university of chicago physicist enrico fermi. create your own fermi estimation problem, give it your best answer, and show us how you got there., – inspired by malhar manek, class of 2028.

Finally, a prompt for the mathematically inclined! The key here is to think of an estimate that is aligned with your interests. If you’re an electrical engineering nerd, maybe you want to estimate the number of circuits in UChicago’s Physics Building. If you love anime, maybe you’ll estimate the number of pen strokes in an episode of your favorite show. If you’re into fashion, perhaps you’ll estimate the number of stitches sewn into Janelle Monáe’s Met Gala gown. As with many questions on your math tests, this prompt asks you to show your work, so be sure to share every step you took to arrive at your answer. Remember, the goal is not necessarily to get the answer right, but rather to learn more about you and how your brain works. Don’t be afraid to get weird!

Essay Option 6

And, as always… the classic choose your own adventure option in the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). be original, creative, thought provoking. draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the university of chicago; take a little risk, and have fun.

We love all the prompts from the past —there are so many quirky ones! If this year’s questions aren’t inspiring you, don’t be afraid to peruse the archives to find one that stands out to you. If you belong at UChicago, there is no doubt you will find a prompt that sparks a story within you. 

We’d also like to note that this is a great opportunity for recycling essays. If you wrote a strong longform essay for another school, see if any of the old prompts work in your favor, or make up your own question custom-built for your essay. Good luck! 😊

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The 7 UChicago Essay Prompts: How to Write Stellar Responses

College Essays

The University of Chicago is famous for its unique essay topics. They're some of the most creative and off-the-wall essay prompts you'll see when applying to colleges, and it can sometimes be confusing to know how to tackle them.

What should you write about in your UChicago essays? How can you show that you're intelligent, creative, and worthy of a place at their school? As someone who spent a long time on my UChicago essays (and who got into the school), I've figured out exactly what UChicago is looking for in these essays.

 Read on to learn all about the UChicago essays, what the admissions team expects to see in your responses, what topics you should write about, and which topics you should avoid. In this guide, we also suggest sample essay ideas for each of the 2022/2023 UChicago supplement essay prompts and analyze past University of Chicago essay samples so you can see what a great UChicago essay looks like.

What Are the UChicago Essays?

Before you can begin figuring out how you'll write your UChicago essays, you should know which prompts you'll be seeing and the rules for each one. You'll need to write two essays, and the UChicago essay prompts you must answer are commonly referred to as Question 1 and Question 2.

Question 1: Why UChicago?

The Question 1 prompt is the only UChicago supplement essay that stays the same each year, and it's also the only prompt that all applicants must answer (for Question 2 you'll have multiple prompts to choose from).

For this question, you'll need to write an essay that explains why you want to attend the University of Chicago and why you think the school is a good fit for you and your goals. UChicago doesn't have strict word limits for essays, but they suggest a response of 1-2 pages.

Here's the prompt:

How does the University of Chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future? Please address with some specificity your own wishes and how they relate to UChicago.

The nice part about this prompt is that it's a pretty standard "why this school" essay . And luckily for you, we have a complete guide that walks you through how to knock this type of essay out of the park.

Question 2: Extended Essay

For Question 2, you have a choice of six essay prompts, and you'll choose the one you want to respond to. The essay prompts for this question change every year, and while there are always around six prompts, some years there may be one more or one less to choose from.

These are the more unique and offbeat essay prompts that UChicago is known for. Many of them were created by UChicago alumni and current students. Again, UChicago asks you submit a response 1-2 pages long.

Below are the essay prompts for the 2022/2023 school year.

Essay Option 2: “Where have all the flowers gone?” – Pete Seeger. Pick a question from a song title or lyric and give it your best answer.

Essay Option 3: “Vlog,” “Labradoodle,” and “Fauxmage.” Language is filled with portmanteaus. Create a new portmanteau and explain why those two things are a “patch” (perfect match).

Essay Option 4: A jellyfish is not a fish. Cat burglars don’t burgle cats. Rhode Island is not an island. Write an essay about some other misnomer, and either come up with and defend a new name for it or explain why its inaccurate name should be kept.

Essay Option 5: Despite their origins in the Gupta Empire of India or Ancient Egypt, games like chess or bowling remain widely enjoyed today. What modern game do you believe will withstand the test of time, and why?

Essay Option 6: And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the University of Chicago; take a little risk, and have fun!

The world is your oyster when it comes to answering UChicago essay prompts.

How to Answer the University of Chicago Essay Prompts

In this section, we explain what UChicago wants to see in your essays, give ideas for topics to write about for each of the essays, and discuss topics you are better off avoiding.

For this University of Chicago supplement essay, UChicago wants to know why you want to attend their school, what you hope to get out of attending, and how University of Chicago will help you achieve their goals. Basically, they want to know why you think their school is a better fit for you than all the other schools out there. For more analysis of this essay, check out our in-depth guide to the Why UChicago essay .

What Do They Want to See in Your Response?

The "why our school?" is probably the most common essay prompt you'll see on college applications. Why do schools, including UChicago, ask this question?

UChicago wants to first see that you really want to go to their school. Students who love a school are more likely to accept an offer of admission and attend it, and they are more likely to be committed to their studies, participate in extracurriculars, and give back after they graduate. Your passion for UChicago should be shining through in this essay.

Next, UChicago wants to see that you've done your research on their school and have an idea of what opportunities you want to take advantage of while there. You can do this by mentioning specific things you like about UChicago or that you plan to take advantage of as a student there. Potential things to discuss include professors you admire or are interested in working with, specific classes you want to take, and extracurriculars you want to participate in.

Finally, UChicago wants to see that you are a good match for their school. Your essay should explain how you'll make the best use of what UChicago offers, how your strengths match the opportunities they provide, and how UChicago will help you reach your goals for the future.

Potential Topics to Write About

There are many ways you could approach this essay prompt; although since UChicago is best known for its academics (as opposed to killer sports teams, for example), most people will discuss the academic side for at least part of their response. Below is a list of possible topics; most people will discuss one to three topics in their essay.

• Majors or classes you're especially interested in
• UChicago's core curriculum
• Professors whose work you admire and whom you'd like to study with or conduct research with
• Unique events like Scav and Kuviasungnerk/Kangeiko
• Research opportunities you'd like to have
• University of Chicago students you've met who you admire
• Volunteer opportunities
• Financial aid opportunities UChicago offers that make it possible for you to attend

Topics to Avoid

The key here is to avoid generic topics that could apply to practically any school or any student. You want it to be clear in your response what opportunities the University of Chicago offers you that no other school does and how you're going to make use of them. Topics that won't show this include discussing:

• How pretty the campus is
• Chicago weather
• The food on campus
• Where UChicago places on college ranking lists
• Your future major and career path without connecting it back to what UChicago offers
• Bashing other schools

The extended essay is when you can get especially creative. These prompts require you to move outside your comfort zone of typical essay topics and answer in a way that gives readers insight into who you are and what you care about. Remember: Question 2 is required, but you have six different prompts to choose from for this essay response.

Your response to Question 1 is meant to show what you like about UChicago and how you’re going to make the most of the opportunities it offers. Question 2 is less about UChicago and more about you. The admissions team wants to see who you are and what's important to you. Three main things they'd like to see in your essay response are:

• Your personality
• Your thirst for knowledge

Who are you? What have been the important events in your life? What kind of person are you? What do you love learning about? These are the questions UChicago wants you to answer. They want to know what's important to you, what events from your past shaped you, what kind of person you are now, and what you want to accomplish in the future. 

UChicago is particularly interested in students who love learning and have a lot of interests in different fields and topics. A mathematician who also does ballet? A creative writing major who started her own business? Bring it on! Make sure to show your love for learning in your essay.

Your passions and goals don't always need to be lofty though; in the second example essay below you can see how the writer took a quirky interest and managed to connect it to larger ideas. If you can connect one of your pet passions to an essay topic, do so!

The great thing about these UChicago essay prompts is you can write about almost anything you want to since they're so different from each other and give you lots of chances to be creative. And you can tackle it from any angle you want. On their website , UChicago states that "[This essay] can be approached with utter seriousness, complete fancy, or something in between." Just remember, you want this essay to give UChicago a good idea of the type of person you are and what's important to you.

Essay Option 1

Exponents and square roots, pencils and erasers, beta decay and electron capture. Name two things that undo each other and explain why both are necessary.

You're allowed to let your imagination run wild with this prompt. You should try to find a pair of objects that the admissions panel didn’t think of, something wholly original that only you would think of. For this prompt, they want to see how imaginative you can be, but the most important part of this essay is justifying why your pairing makes sense and why it matters . The pair you choose will show off your personality, creativity, and cultural experiences. 

Make your response as wacky and original as you like, but remember to tie it back to yourself and your interests a nd/or potential major. For instance, say you go with the idea of an art conservator and the passage of time. You could discuss how time degrades the materials of a work of art, and then an art conservationist revitalizes the work, only to have the passage of time wear it down again. This would be an excellent segue into writing about your interest in history, creative writing, or U Chicago’s Department of Art History Conservation Science Teaching Program . 

You could also write about how you developed an interest in these subjects, and what other interests you have could be applicable . Weaving your story into your essay will show UChicago that you’re creative and intellectually curious. This can include your niche interests, quirky hobbies, or pet projects.

Essay Option 2

“Where have all the flowers gone?” – Pete Seeger. Pick a question from a song title or lyric and give it your best answer.

This is a classic UChicago question that allows you to answer the question literally...or not. (The year I applied, the version of this question was "Describe your table.") So, if this exemple were your actual song lyric, you address, where have all the flowers gone? You could answer this literally and describe how, for instance, flowers are changing colors in response to climate change . Perhaps you could then discuss your interest in horticulture and what led you to pursue that field.

Or (as always with UChicago essays), you can take it in a totally unexpected direction. This prompt is a chance to put your interpretive and reasoning skills into action. In fact, you could almost think of it like a riddle, except that the answer is anything that you can come up with and justify:

“Where Do Broken Hearts Go?” A valid question in a world where loneliness has been declared a public health emergency and social isolation can increase the likelihood of heart disease by as much as 29% ! 

“Do You Remember Rock and Roll Radio?” Likely not, considering radio listening has been trending downward for years, especially amongst young listeners and Rock Music is at the lowest point in its popularity since about 1960 . Where does this leave you, a young would-be guitar player with an interest in U Chicago’s ethnomusicology program ?

“Do You Really Want to Hurt Me?” Perhaps you do, considering recent studies show a decline in empathy and corresponding rise in narcissism .

You get the idea. Whatever question you choose, don’t worry too much about having a great answer for it; the idea is to find a context for the question that is meaningful to you and relates to your interests , which will give UChicago insight into your values and personality, two things they want to see in these essays!

Essay Option 3

“Vlog,” “Labradoodle,” and “Fauxmage.” Language is filled with portmanteaus. Create a new portmanteau and explain why those two things are a “patch” (perfect match).

This prompt is a bit sillier, but you still have the chance to show U Chicago your personality and unique worldview. This prompt gives you a chance to play with language and create something that expresses a meaning that we don’t have a word for. The best way to go about this is to think of two areas that are important to you and find a pair of rhyming words related to each and combine them.

So, for instance, if you’re math-oriented but somewhat spiritual, you could take words from both mathematics and spirituality, and come up with something like “stamystics” (statistics+mystics). You could talk about how you became interested in math and how it relates to your spirituality, and so forth.

If you are more interested in sports than spirituality, you could come up with something like “mathleticism.” You could write about how you had to train your mind in order to grasp difficult or advanced mathematical concepts and, inversely, how your understanding of math deepens your appreciation of sports.

What U Chicago is looking for here is how you can connect two seemingly unrelated concepts and find a bridge between them. They’re looking for problem-solving in addition to insight into your personality.

Essay Option 4

A jellyfish is not a fish. Cat burglars don’t burgle cats. Rhode Island is not an island. Write an essay about some other misnomer, and either come up with and defend a new name for it or explain why its inaccurate name should be kept.

This prompt gives you an opportunity to think about familiar things in a new way. We probably don’t think much about peanuts not being nuts, but it’s obvious once you think about it that they are legumes. But, on the other hand, they are also closely related to peas–so the name has some validity. Even though they’re not actually nuts, they do taste like nuts…so is it wrong to call them nuts? Think about other examples that exist in your fields of interest.

And of course, be sure to let your experiences, interests, and values shape the way you rename or defend your misnomer . That way, UChicago will get a good idea of who you are and what’s meaningful to you!

Essay Option 5

Despite their origins in the Gupta Empire of India or Ancient Egypt, games like chess or bowling remain widely enjoyed today. What modern game do you believe will withstand the test of time, and why?

This prompt is your chance to be more overtly academic in your response . In writing about how this game will remain relevant in the future, you’ll be able to show your knowledge of history, culture, politics, economics, religion, scientific discovery…and so on! Choose a game that interests you in some way that you can tie into your personal history and academic interests. 

While brainstorming possible games will be really fun, the most important part of this essay is justifying why you think something that’s relevant today will continue to be relevant in the future. Think about what cultural, social, and political changes could be possible and what the implications of that could be for people today. As long as you’re creative, descriptive, and thorough, your response can range from serious to silly and meet the requirements for this prompt.

Essay Option 6

And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the University of Chicago; take a little risk, and have fun!

If you aren't feeling any of the other five optional prompts, you can respond to this one, which asks you to choose and respond to a past UChicago optional essay prompt, or write and respond to your own prompt. With either option, you'll want to consider your identity, interests, strengths, and goals, and let those factors inform which prompt you choose, how you write your own prompt, and how you craft your response.

You may not feel up to the task of writing your own prompt, but you might like the idea of tracking down an old prompt that catches your eye. Read through the past prompts and consider which one will allow you to play to your strengths . If there's a particular experience or skill that you want to showcase in your response, select a prompt that is conducive to that.

Alternatively, if there's a specific experience you want to write about, you can write your own prompt and respond to it. To write your prompt, use the tone and structure of the existing UChicago prompts as a guide. It'll probably come as no surprise that your original prompt should fit right in with the ones provided on the application. This means you might have to be a little goofy, cryptic, or risky...and that's a good thing!

Though this option allows you to write your own prompt if you so choose, it's important to remember that your response to the prompt should still focus on showcasing who you are , what strengths you will bring to UChicago as a student, and why UChicago is the perfect place for you. Don't get too carried away trying to impress admissions with punny phrases or cryptic logic; be authentic, be bold, and be you.

Some people shy away from this prompt because they feel like it's "cheating" or less impressive to not follow one of the specific prompts that UChicago gives. However, this isn't true! As long as you write a compelling essay that gives readers a better insight into who you are, your essay will strengthen your application. For what it's worth, when I applied to UChicago, this is the prompt I chose, and I was still accepted to the school.

UChicago wants you to be creative here, so there aren't many topics that are off limits. However, you're trying to convince them that you'd be a great and interesting student to add to their school, so make sure you use your essay to show who you are and why UChicago would want to admit you.

This means you should avoid responses that don't give readers a good idea of who you are. For example, if you choose essay option 1, don't just state that “taco cat” is funny because it reminds you of your favorite meme. Instead, tie it back to yourself and your life by explaining its relevance, like making tacos with your abuela and fending off the family cat’s attempts to steal tacos. 

Because these prompts are creative, it can be easy to run away with them, but always remember to answer the prompt completely and give UChicago better insight into who you are.

Additionally, don't feel that certain University of Chicago essay prompts are "better" or more impressive than others . UChicago wouldn't have chosen these essay topics if they didn't think applicants could write outstanding responses to them, so please choose the prompt that you feel you can write the best essay for.

University of Chicago Essay Examples

In this section are two University of Chicago essay examples, each written by an accepted applicant.

Below each UChicago supplement essay we discuss what makes the essay work so well.

Dear University of Chicago,

And now you inquire as to my wishes? They're simple, accept me for who I am! Why can't you just love and not ask why? Not ask about my assets or my past? I'm living in the now, I'm waiting for you to catch up, but you're too caught up in my past, I offer us a future together, not a past to dwell upon. Whenever I'm around you, I just get that tingle deep inside me that tells me you're the one; you have that air of brilliance and ingenuity that I crave in a person, you're so mature and sophisticated, originality is really your strongest and most admirable trait. I wish we could be together, I still think in my heart of hearts we were meant to be, but you have to meet me halfway, dear. I'm on one knee here with tears welling up in my eyes, the fireworks are timed and ready to light up the night sky for you, just say 'I accept...you.'

Why Does This Essay Work?

• Creative take on a standard prompt: The writer chose a very unique angle for this essay: comparing the University of Chicago to a lover. He's probably the first applicant to answer the essay prompt this way, which definitely makes this a memorable essay. In fact, UChicago loved this essay so much that they mailed it out to thousands of potential applicants (which actually got them a bit of backlash ). You absolutely don't have to take as unique an approach to this essay as the above writer did, but doing so can definitely help your essay stand out.
• It answers the entire prompt: Even though this is an unusual essay, the writer still manages to answer everything the prompt asks for. He mentions his goal for the future (to become a lawyer), mentions varied interests he has (the Gothic era, the philosopher Kierkegaard), and explains what he likes about UChicago (the brilliance, ingenuity, and originality the school offers). He even manages to mention that he visited campus three times, which shows a serious interest in the school. If you choose to write an especially offbeat essay, it's key to do what this essay did and still answer the prompt while being creative.

This essay is from several years ago, so it doesn't use a current prompt, but it's still helpful to read and analyze.

Share with us a few of your favorite books, poems, authors, films, plays, pieces of music, musicians, performers, paintings, artists, blogs, magazines, or newspapers. Feel free to touch on one, some, or all of the categories listed, or add a category of your own.

Now let's take a look at the successful essay:

The Illuminati changed my life. Three years ago, I found my first ambigram in one of my favorite novels, Angels and Demons by Dan Brown. I turned the page, and there it was: the word "Illuminati" printed into the exact center of the book. It was styled like a newspaper masthead, exquisite and complex, yet oddly symmetric. Curious, I rotated the book upside-down.

Impossibly, the inverted word was still "Illuminati." Gazing closer, I realized that the letters, I-L-L-U-M, actually shaped into a flipped I-N-A-T-I. Suddenly, I was reading it in both directions. My eyes waltzed along the broad curves and sharp twists of the calligraphy, striking poses in a glamorous font against a sheet of creamy whiteness, sliding between the dense vertical strokes, peering at the edge of the defined serif as it angled away, then bent boldly toward me. Every line was deliberate, every flourish smiling with purpose, and the whole word balanced on the delicate cord that joined two letters into one. It was unforgettable.

Ambigrams are words that can be read from different directions. Actually, "ambigram" is an umbrella term that encompasses dozens of distinct types of visual wordplay. The most popular ones are rotational, mirror image, and-my personal favorites-symbiotic ambigrams, which can spell two different things when viewed normally and upside-down.

Compelled by the striking art, I could not help but try my own hand at designing ambigrams, and slowly I felt the pitiful stick-figure artist inside me shrink away as my inner energetic graphic designer sprang up. Before early volleyball tournaments, I work myself up by filling up pages and pages of experimental letter combinations, gleefully satisfied at the way that a rounded lowercase "a" was a perfect upside-down lowercase "e." In my AP Literature class, I drew "She's a witch!" which revealed, when flipped, "Communist" to reflect Arthur Miller's contemporary motives for writing The Crucible. On a challenge from a friend, I even drew an ambigram of "Jay-Z" and "Beyonce" on a bumpy bus ride back from a leadership retreat.

In the last few months, I have also practiced drawing ambigrams as fast as I can. I dream about the day when I can effortlessly write out a message saying "Hi, how are you today?" normally and "The password is cherry268" upside-down, without pausing or rotating the paper. I imagine a world in which everyone had this ability, and could literally write two things at once. How would that change communication? Encryption? Trust? My legs swing comfortably from this innovative edge, excited to take a stab at the answers.

The best part about the ambigram is that it refuses to define itself as just one thing. It is a linguistic passion, a cryptographic endeavor, an artistic design, and an ironic illusion. I relish the fact that ambigrams force both the artist and the audience to reject first glances and embrace secret identities.

This may just be a nerdy obsession, but ambigrams have taught me far more than how to sketch fancy words. Their multidimensional truth implies that my hobbies of both writing Italian sonnets and solving logical riddles are not opposing functions of my left and right brains, but rather, a perfect conglomeration of my passion for creating and solving puzzles. The beauty of the most surprising combinations reminds me to take bold risks in both my life and my designs.

Above all else, ambigrams have taught me that I can create the impossible. I can make true and false the same word depending on something as simple as a 180-degree head turn. Victory can be defeat. Open can be closed. Am amateur piano player with an obsession for cryptology can learn how to program iPhone apps and get the game-winning kill at the varsity volleyball championship. A girl with divorced parents can make time for both families, and an inspired teenager from California can write her name into world history--both normally and upside-down.

- Samantha M.

Why This Essay Works

• Shows passion: This essay focuses on a pretty unusual and specific topic: ambigrams. While many people may not even know what an ambigram is, the writer is clearly passionate about them. She discusses how much time she spends trying to create different ambigrams, what her goals for ambigram creating are, and some of her favorite ambigrams she's created. UChicago loves people who are passionate about something, even if it's an unusual or offbeat interest. It makes UChicago believe those students will bring that passion with them onto campus.
• Gives insight into the writer's personality: The majority of this essay is about the author's interest in ambigrams, but she also manages to cleverly slip in multiple other references to her personality and interests. From her essay, we learn that she's a volleyball player, writes Italian sonnets, and loves solving puzzles. Adding these details gives UChicago a fuller look at what makes her tick.
• Connects it to a bigger picture: The writer chose to write about a very specific topic—ambigrams—but was still able to connect that to bigger concepts, such as communication, truth, and how she's able to balance her different interests. She's able to take a quirky topic and show how it influences her worldview.

Final Advice: UChicago Essays

When answering the University of Chicago essay prompts, keep in mind that the main reason UChicago is reading these essays is to find out who you are as a person and if you'd be a good fit at their school.

The University of Chicago wants students who are passionate about learning, creative, are excited to make the most of their time on campus, and have big dreams for themselves, and the UChicago supplement questions are designed to help you show these sides of yourself to the school.

For the "Why UChicago?" prompt, you'll want to show the school why you want to go there, why you think you're a good fit for the school, and how UChicago will help you achieve your goals during college and beyond.

For the extended essay, you can (and should) be more creative. These UChicago essays are more "out there," and in your response, you should show your personality and passion for learning.

For both University of Chicago essays, remember to show who you are and what you're passionate about, include details about yourself and the school to help you stand out from other essays, and mention your plans and goals for the future.

What's Next?

If you want a more in-depth look how to write about Question 1, check out our guide to the Why UChicago Essay , which includes an additional sample essay along with analysis of how to answer this prompt.

Are you working on the Common App essay ? Read our breakdown of the Common App prompts and our guide to picking the best prompt for you.

If you're planning to take the SAT or ACT one last time , try out some of our famous test prep guides, like "How to Get a Perfect Score on the SAT" and "15 Key ACT Test Day Tips."

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Christine graduated from Michigan State University with degrees in Environmental Biology and Geography and received her Master's from Duke University. In high school she scored in the 99th percentile on the SAT and was named a National Merit Finalist. She has taught English and biology in several countries.

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University of Chicago’s 2023-24 Essay Prompts

Select-a-prompt essay.

Choose one of the seven extended essay options and upload a one- or two-page response. Please include the prompt at the top of the page.

Exponents and square roots, pencils and erasers, beta decay and electron capture. Name two things that undo each other and explain why both are necessary. —Inspired by Emmett Cho, Class of 2027

“Where have all the flowers gone?” – Pete Seeger. Pick a question from a song title or lyric and give it your best answer. —Inspired by Ryan Murphy, AB‘21

“Vlog,” “Labradoodle,” and “Fauxmage.” Language is filled with portmanteaus. Create a new portmanteau and explain why those two things are a “patch” (perfect match). —Inspired by Garrett Chalfin, Class of 2027

A jellyfish is not a fish. Cat burglars don’t burgle cats. Rhode Island is not an island. Write an essay about some other misnomer, and either come up with and defend a new name for it or explain why its inaccurate name should be kept. —Inspired by Sonia Chang, Class of 2025, and Mirabella Blair, Class of 2027

Despite their origins in the Gupta Empire of India or Ancient Egypt, games like chess or bowling remain widely enjoyed today. What modern game do you believe will withstand the test of time, and why? —Inspired by Adam Heiba, Class of 2027

There are unwritten rules that everyone follows or has heard at least once in their life. But of course, some rules should be broken or updated. What is an unwritten rule that you wish didn’t exist? (Our custom is to have five new prompts each year, but this year we decided to break with tradition. Enjoy!) —Inspired by Maryam Abdella, Class of 2026

And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the University of Chicago; take a little risk, and have fun!

Why This College Essay

How does the University of Chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future? Please address with some specificity your own wishes and how they relate to UChicago.

Common App Personal Essay

The essay demonstrates your ability to write clearly and concisely on a selected topic and helps you distinguish yourself in your own voice. What do you want the readers of your application to know about you apart from courses, grades, and test scores? Choose the option that best helps you answer that question and write an essay of no more than 650 words, using the prompt to inspire and structure your response. Remember: 650 words is your limit, not your goal. Use the full range if you need it, but don‘t feel obligated to do so.

Some students have a background, identity, interest, or talent that is so meaningful they believe their application would be incomplete without it. If this sounds like you, then please share your story.

The lessons we take from obstacles we encounter can be fundamental to later success. Recount a time when you faced a challenge, setback, or failure. How did it affect you, and what did you learn from the experience?

Reflect on a time when you questioned or challenged a belief or idea. What prompted your thinking? What was the outcome?

Reflect on something that someone has done for you that has made you happy or thankful in a surprising way. How has this gratitude affected or motivated you?

Discuss an accomplishment, event, or realization that sparked a period of personal growth and a new understanding of yourself or others.

Describe a topic, idea, or concept you find so engaging that it makes you lose all track of time. Why does it captivate you? What or who do you turn to when you want to learn more?

Share an essay on any topic of your choice. It can be one you‘ve already written, one that responds to a different prompt, or one of your own design.

What will first-time readers think of your college essay?

What are your chances of acceptance?

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How to Write the University of Chicago Essays 2023-2024

The University of Chicago is famous for its unconventional supplemental essay prompts, and this year is no exception. While there is one traditional prompt that asks you to write about your interest in UChicago, the star of your essay package will be your response to one of seven incredibly outside-the-box prompts (with the seventh being a choose your own adventure).

Because the brainstorming you’ve done for all your other college essays is unlikely to help much here, you want to make sure you leave yourself extra time to really give these prompts the attention they require. One thing you’ll quickly realize is there’s no way to “brute force” your answer—you just need to be patient and let your ideas develop.

In this post, we’ll break down each prompt for you, so that, while you’ll still have to harness your own creativity, you can be confident in your overall approach.

Read these UChicago essay examples to inspire your writing.

Before You Begin Writing  

The University of Chicago’s prompts are famous (infamous? both?) for being different, quirky, and sometimes downright weird. Have you ever seen the word cheese or pie in a college essay prompt before? I’m guessing not. But don’t get discouraged or overwhelmed—the weirdness of the UChicago prompts makes them ripe with opportunity to explore your passions, interests, and personal oddities. 

You know that subject you avoid in casual conversation, because it turns you into a gushing ball of enthusiasm that could talk for hours ? UChicago wants to hear about it. Whether it’s feminist literature of Southeast Asia, modern perception of African art, or your job at Colonial Williamsburg, UChicago has happily passed you the mic. 

While your creative opportunity has few bounds, there are some key strategies to conquering the UChicago essays. Keep this checklist of things in mind as you write: 

Unconventional topics often require unconventional styles. 

UChicago essays should definitely be viewed as a piece of creative writing, rather than a dry analysis. When you are in college, you will be asked to write thesis-driven essays, but that’s not what the UChicago essays are asking for. You need to have a clear focus, but you should be comfortable disrupting the familiar rhythms of essay prose. This can mean vivid (and I mean vivid ) imagery, addressing the reader directly, sentence fragments, CAPS, lists, and anything else! Toss in some wild jargon from your field, phrases from another language, anything you’ve got—as long as you explain them. You should try to be imaginative, engaging, and colorful while maintaining an authentic voice and staying focused with your subject matter.

Communicate who you are as an academic.

The point of your essay is still to tell admissions officers about yourself. Give them an image of how you will perform in and contribute to an academic environment. You can’t just gush about your topic—you have to prove that you can engage with it at a highly intellectual level. Explain research protocol, cite specific books you’ve read, mention your AP and IB classes, or give examples of how you’ve collaborated with others to produce results. 

UChicago admissions don’t want a student who says “I love physics”; they want a student who says “I love physics so much that I stayed up until 4 am reading Cosmos by Carl Sagan, and I use meatballs to diagram the moons of Jupiter to my friends, and I took Calc III because I plan on studying mechanical engineering with a focus on aerospace materials.” Be detailed about your studies; be explicit in your interests. 

Marry yourself to your topic.

Be sure to include the first person; you are the main character here, not whatever subject you’re writing about. The subject is an avenue to tell admissions officers about you. You aren’t trying to get your latest film, your famous lasagna, or your community service project into the university— you are trying to get in . Don’t be afraid to center yourself. How do these objects from your past illuminate facets of your personality? What do your interests say about you ?

And, as always, answer the prompt!

Print out the prompt, circle key words, hang it on your mirror. Read it, then read it again, and again . Sit with the prompt, get some (probably crazy!) ideas, then repeat the process! Many UChicago prompts are dense in their weirdness. Some of them take time to even understand. Many prompts will reveal themselves to you in your everyday life (after you’ve read them over and over again). Some of them just take deep thought. The key is to keep thinking and focus on what the prompt is asking. You’ve got this!

All the UChicago Essay Prompts

Prompt 1: (required), how does the university of chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future please address with some specificity your own wishes and how they relate to uchicago., prompt 2: extended essay (required; choose one).

Option A: Exponents and square roots, pencils and erasers, beta decay and electron capture. Name two things that undo each other and explain why both are necessary. —Inspired by Emmett Cho, Class of 2027 

Option B: “Where have all the flowers gone?” – Pete Seeger. Pick a question from a song title or lyric and give it your best answer. —Inspired by Ryan Murphy, AB’21 

Option C: “Vlog,” “Labradoodle,” and “Fauxmage.” Language is filled with portmanteaus. Create a new portmanteau and explain why those two things are a “patch” (perfect match). —Inspired by Garrett Chalfin, Class of 2027 

Option D: A jellyfish is not a fish. Cat burglars don’t burgle cats. Rhode Island is not an island. Write an essay about some other misnomer, and either come up with and defend a new name for it or explain why its inaccurate name should be kept. —Inspired by Sonia Chang, Class of 2025, and Mirabella Blair, Class of 2027

Option E: Despite their origins in the Gupta Empire of India or Ancient Egypt, games like chess or bowling remain widely enjoyed today. What modern game do you believe will withstand the test of time, and why? —Inspired by Adam Heiba, Class of 2027 

Option F: There are unwritten rules that everyone follows or has heard at least once in their life. But of course, some rules should be broken or updated. What is an unwritten rule that you wish didn’t exist? (Our custom is to have five new prompts each year, but this year we decided to break with tradition. Enjoy!) —Inspired by Maryam Abdella, Class of 2026 

Option G: And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the University of Chicago; take a little risk, and have fun!

The pressure’s on to be unique here, since EVERY SINGLE APPLICANT to UChicago will be answering this required question. Here’s what you need to do:

Provide a tangible connection to UChicago. 

This is composed of specific elements of the university that appeal to you, and UChicago’s website is a great place to delve into these. Be sure to be “particular,” as they stipulate, and give them the “specificity” they’re asking for. Examples include research opportunities at Argonne Labs, the marketing classes in the Business School, or an internship offered through the Creative Writing program. 

Don’t write about UChicago’s general attributes, like fame, prestige, or “intellectual rigor.” And please don’t try to be clever and refute the old canard that UChicago is the place “Where Fun Goes to Die.” Application readers have seen this hundreds, if not thousands of times. And besides, why talk about a tired UChicago stereotype when you can talk about something cool? 

Describe your intangible connection as well. 

How is UChicago a place that aligns with your values, dreams, and goals? How do you vibe with it? For example, if I wanted to write about the Creative Writing internship, I would state explicitly how it draws me in: 

“ I want to attend a college that values the innovative nature of indie comics publishing as much as I do. So, I’m impressed by UChicago’s commitment to providing internships in comics writing through Bult Publishing and The Artifice magazine. One of my goals as a writer is to gain firsthand experience in comics publishing, specifically small houses, and the Creative Writing program at UChicago hits the mark, resoundingly. ”

Engage with faculty and students, if possible. 

This is a perfect place to talk about specific interactions, like sitting in on an inspiring seminar during a campus visit, hearing a professor speak, or seeing how UChicago has prepared a friend for his career. 

However, always be sure to tie these experiences into your own goals and interests! For example, don’t just name-drop a certain Professor Smith. Instead, take the opportunity to find a personal connection to Smith’s research and how great UChicago is for supporting people like her. Your format should be

        Program/Individual/Major – UChicago’s Values – My values

If you want to learn more about a specific professor or their subject, don’t be afraid to politely email them or contact their department. Many love to talk about their work and their interests, or would love to put you in touch with current students. This will better inform you about the school and give you a great edge for this prompt. And, more importantly, you’ll probably get great advice for your higher education journey. Note: the earlier you prepare for this, the better!

It’s worth noting that there is no recommended essay length, but sticking to around 500 words should do the trick. It’s long enough to share the reasons you’ll thrive at UChicago, but not too long that the admissions officers will start to get bored.

Prompt 2: Extended Essay (Required, Choose One)

Choose one of the six extended essay options and upload a one- or two-page response. Please include the prompt at the top of the page.

Prompt 2, Option A

Exponents and square roots, pencils and erasers, beta decay and electron capture. name two things that undo each other and explain why both are necessary. —inspired by emmett cho, class of 2027.

Brainstorming Your Topic

You’ll notice with UChicago’s prompts that, while unusual, they are usually quite specific in what they want you to write about. The challenge is that the category is likely not something you’ve ever spent much time thinking about, so figuring out what you want to write about will take a lot more effort than, for example, explaining what a particular extracurricular activity has meant to you.

Here, one thing you have going for you is that the examples UChicago provides of “undoers” cover a pretty wide range of things. You can write about a sophisticated pair, like beta decay and electron capture, but you can also write about something as familiar as pencils and erasers.

Because of this flexibility, a good place to start your brainstorming is by thinking of some of your interests, and then trying to identify a pair of undoers related to that interest. For example, maybe you’ve always really enjoyed doing your hair and makeup. A curler and a straightener would absolutely work as a topic for this prompt. Alternatively, if you’re interested in anatomy, you could write about systole and diastole, the contraction and relaxation of the heart.

If this approach isn’t getting you anywhere, zoom further out, and think about everyday activities and objects, to see if that sparks an idea. For example, maybe you’re wandering around your house, and see your mother’s old sewing kit, which inspires you to write about scissors and thread. Or perhaps you’re thinking about your commute to school, and you realize drive and reverse would work.

Remember that the whole point is to be creative. Don’t worry about what UChicago admissions officers “want” to see, because honestly, they aren’t trying to angle you in a certain direction. If they were, they wouldn’t give you a prompt that was so difficult to brainstorm for. So if something comes to your mind that you feel excited about, run with that—don’t get in your own way by asking yourself if it’s “good enough.” As long as you’re inspired, the answer to that question is a resounding “yes.”

Tips for Writing Your Essay

The goal of your brainstorming process is to pick “two things that undo each other.” Once you have them, you can move on to drafting your actual essay, where your goal is addressing the second half of this prompt: “explain[ing] why both are necessary.”

Although UChicago doesn’t say it outright, the key to a strong response is reading the word “necessary” through a philosophical lens. UChicago doesn’t want you to literally explain why a car needs to have both drive and reverse. That approach would lead to an overly academic-feeling, dry essay, as it’s obvious why a car needs to be able to move forwards and backwards, and remember, the point of this essay is to show off your creativity.

Rather than being literal, you want to think of how you can use your undoers to make a deeper point about how you see the world. UChicago may choose unusual packaging, but this is still a college essay, so the point is ultimately to teach admissions officers something about yourself, so that they can better envision you as a member of their campus community.

Obviously, there’s no one right way to do that, but a good place to start is by thinking of how you might connect your undoers to a story from your own life. Again, this is still a college essay, and relying on specific examples (and using descriptive writing to flesh out those examples) will make your response much more engaging to read.

For example, maybe you focus your essay on a road trip your family took when you were little, and talk about how, without reverse, you would never be able to return to the places you visited where you made such fond memories, but without drive, you wouldn’t be able to continue exploring new destinations. 

You could even get more creative than that, if you’re feeling so inspired, as UChicago sets no rules for how you need to structure your response. So, to run with a different example from the “Brainstorming” section, maybe you talk about how when the heart contracts and sends blood circulating through the body is when you feel connected to the world, and can better understand the great writers of history like Shakespeare, Lao Tzu, and Ovid. When the heart relaxes, on the other hand, is when you retreat into your own thoughts, and wonder about how you can leave your own mark on this tiny planet spinning through the blackness of space.

Your approach will likely look completely different from both of these examples, but hopefully they at least help get your gears turning by giving you some general thoughts about how you might set up the “this and that” dynamic. 

Mistakes to Avoid

Pretty much the only thing we’d encourage you not to do is write about one of the pairs of undoers UChicago lists in the prompt. You may be tempted to, either because you genuinely feel a connection to one of them, or because you’re just suffering from terrible writer’s block and can’t think of anything else.

Remember, though, that the point here is creativity, so using an example UChicago came up with for you will be a letdown for admissions officers. Plus, as with any college essay, you want your response to set you apart from other applicants, and there will likely be a good number of other students who end up settling for one of the examples provided.

If you really are completely stuck, we have good news for you—there are six other prompts you can choose from here! While still unusual, of course, hopefully you’ll feel more of a kinship with one of them than you do with this one.

Prompt 2, Option B

“where have all the flowers gone” – pete seeger. pick a question from a song title or lyric and give it your best answer. —inspired by ryan murphy, ab’21.

If music is a big part of your life, either because you play an instrument or sing yourself, or because you are a fan of a certain style of music or even a particular artist, you may feel immediately drawn to this prompt. Maybe you even already have a line in mind that you want to focus your essay on.

However, you can also write a strong response to this prompt even if you have no musical experience whatsoever. The lyric or song title is just the leaping off point for the essay—the points you make can be totally unrelated to music. The only thing to be aware of is that, if you have a more limited musical background, brainstorming may take a little longer, as you’ll have to do more work to think of possibilities.

Regardless of your experience with music, or lack thereof, once you decide that you’re responding to this prompt the best place to start your brainstorming is with artists or songs you already enjoy listening to. Even though, as noted above, the lyric/title is just your starting point, the beginning of your essay will be much more engaging if you already have some sort of connection to it. Genuineness is one of the biggest things admissions officers are looking for in evaluating essays, and that’s a quality that’s impossible to fake. If you just google “famous songs with questions in the title,” your essay may start off feeling dry or impersonal.

Instead, open up your Spotify “On Repeat” playlist, and see if any of the songs there have a question in the title or the lyrics. If none of them do, turn to some of your old favorites, and scan those.

Ideally, the song you choose will already reflect something about you, both because that personal connection will, as noted above, make your essay more engaging to read, and, just as importantly, because it’ll make it more fun for you to write. Here are some examples of how your brainstorming process could go, to hopefully help get your own gears turning:

• Your parents always insisted on playing the oldies radio station when driving you to school, so you pick the line “Will the farmer push the pen, will the writer pull the plow?” from Elton John’s “Lady What’s Tomorrow.” 
• You’re a huge Taylor Swift fan, so you decide to write about her cryptic line “Do you really want to know where I was April 29th?” from the song “High Infidelity.” 
• You have a niche artist you really like, like the Swedish singer Isak Danielson, and so you choose the line “Wouldn’t you say there’s a light in the darkest moment?” from his song “Always.”

Keep in mind that literally every song is available to you, so don’t be afraid of picking a lyric that may seem silly or “out there.” For UChicago, the more unconventional your response, the better. So, if you loved the Barbie movie, you can absolutely write your essay about the line “Is it my destiny to live and die a life of blonde fragility?” from Ryan Gosling’s climactic performance of “I’m Just Ken.”

Also keep in mind that you don’t have to go with the first question you find. In fact, we would suggest not doing that, unless that question really speaks to you. You want to be sure that the question you choose can support a pretty lengthy response to it.

To ensure your question works, we would encourage you to keep a list of possibilities, and once you have 5-10, think more deeply about each one, and how you would structure an essay responding to it. Whichever one makes you feel most excited/inspired is likely your golden ticket.

The number one thing to focus on in writing your actual essay is answering your question in a way that teaches UChicago admissions officers something about you. While, like with all of these prompts, creativity is a strength, this isn’t your journal, nor is it a philosophical treatise. It’s a piece of reflective writing that will hopefully help you gain acceptance to an excellent university.

To ensure your answer to the question is not merely interesting, but also contains information about your personality, think about connections between your own life and the line you’ve selected. These connections can be on the abstract side, so long as you’re confident in your writing abilities, as you’ll need to be able to explain them in a way that your readers will be able to understand. 

If you’re not sure you’ll be able to do that, we recommend sticking to more straightforward connections, as a simple essay that your reader can follow is much better than a complicated one that they can’t. To give you a general idea of how you can relate your own life to your song title/lyric, here are some examples of both simple and more complex connections you could make to the sample lyrics listed in the “Brainstorming” section above:

Simple Connections:

• You like to write, and you also like to garden, so you write an essay about how people are complicated, and can have a wide range of seemingly dissimilar skills and interests
• April 29th is your grandfather’s birthday, so you decide to write about all the wonderful celebrations you’ve had on this date when visiting him at his home in Maine
• You write about how your favorite part of any holiday is the light-up decorations on people’s houses, as they provide light even during the darkest parts of the year, and describe some of the best decorations you’ve ever seen
• You have very delicate blonde hair, and finding the right shampoo has been a lifelong odyssey, so you decide to describe some of the most humorous moments in that saga

Complex Connections:

• You write a satirical piece about a writer and farmer swapping jobs for a day, and their frustrations as they try to learn new skills, and use these characters’ interactions to flesh out some of your own opinions about the world
• April 29th is 4/29 numerically, and 29-4 is 25, while 29+4 is 33, so you write about where you see yourself being at these ages
• You love physics, so you take “darkest moment” literally, and write about black holes, from which, famously, not even light can escape, and write a fairy tale, incorporating moments from your own life, about a photon being chased across a fictional kingdom by a massive, evil black hole
• You write about the fragile “blonde” things you observe in your daily life, like a fallen yellow leaf in autumn, a delicate piece of honeycomb, and winter sunlight glinting on freshly fallen snow, and what you can learn from these things

As you can see from these examples, whether you go with a simple or complex connection, your approach can be either serious or more on the playful side. While neither is automatically better than the other, we do encourage you to have the courage to at least try something a little more lighthearted. College applications are by their nature mostly pretty dry affairs, and mixing up your tone can do a lot to liven things up and help admissions officers stay engaged. 

That being said, it’s crucial that your response feels natural and cohesive, so if the only ideas coming to your mind are more along the lines of the classic, reflective college essay structure, that’s completely fine. As noted above, the strength of your essay is determined by how much it teaches your reader about you, not by the particulars of topic, structure, or any other “nuts and bolts” detail.

The only real rule when selecting a song title or lyric is one that applies to every college essay: don’t choose one that includes profanity, or that references sex, alcohol, or other “adult” topics. While there’s nothing wrong with enjoying that kind of song in your free time, remember that applying to college is a formal process, so you want to come across as respectful and professional.

In terms of writing your actual essay, you want to be sure that you actually answer the question you’ve selected, even if you do so in an unconventional way—that is the whole point of the prompt, after all. So long as you follow our general brainstorming blueprint, and use your question as a narrow lens to scan your memories and experiences, you shouldn’t have issues with your ideas coming untethered from the question. But still take care that it doesn’t happen accidentally. 

For example, say you write all about your grandfather’s birthday celebrations, but forget to mention what date his birthday is. That’s only one missing line in a one- or two-page essay, but without it, UChicago admissions officers will have no idea what’s going on. So, make sure that somewhere, ideally early in the essay, you clearly and obviously connect the question to your broader ideas and experiences.

Prompt 2, Option C

“vlog,” “labradoodle,” and “fauxmage.” language is filled with portmanteaus. create a new portmanteau and explain why those two things are a “patch” (perfect match). —inspired by garrett chalfin, class of 2027.

When you start thinking about possible portmanteaus, your initial thought may be to begin with more examples of existing ones, like “brunch” or “spork.” We would encourage you, however, to shy away from this instinct. Your job here is to create a new portmanteau, and if you start combing through lists of existing ones, you may have trouble getting those out of your head.

Instead, as we’ve recommended in the “Brainstorming” sections of the previous prompts, turn to your own interests and experiences. Like the other prompts, this should still be an essay about you, and you’ll have a hard time with that if you’re combining two words that you have no personal connection to.

Of course, that doesn’t mean you can’t be creative. Even if you look at the well-known examples given, there’s no real reason that, for example, cross-breeding a labrador and a poodle would necessarily result in an extremely popular new breed. Now, labradors and poodles are both kinds of dogs, so there was a pre-existing connection between these two things. But as you come up with your own portmanteau, keep in mind that the two things you combine don’t have to be obviously related. Unlike the examples given, this word probably won’t ever be used by anyone else, so the “patch” only needs to make sense to you.

For example, maybe one of your favorite memories is when a blizzard canceled school, but you and your soccer teammates met up at practice time anyways, and played “snoccer” for two hours. Snow and soccer are not obviously related—quite the opposite, in fact, as sports games are sometimes canceled because of snow. But because of your personal connection to the topic, this portmanteau will undoubtedly be able to support a strong essay.

Or maybe you are most content when knitting with your cat sleeping in your lap, and you decide to explore this feeling of comfort with the new portmanteau “knitten.” Or, to give an example of two more obviously related things, maybe apples and cinnamon is your all-time favorite flavor combination, so you decide it needs an official name, “applemon.”

In your actual response, your job is to follow the prompt, and explain why you see the two things you’re combining as a perfect match. As we’ve already touched on in the “Brainstorming” section above, your explanation should draw on your own personal experiences. UChicago admissions officers don’t want an academic essay on the chemical reactions that make apples and cinnamon such a satisfying flavor combination. 

Rather, they want to hear about how your life was changed the first time your grandma made you apple and cinnamon doughnuts, and how, since then, your mission in life has been to combine the two flavors in as many different forms as possible—not just baked goods, but also cider, jam, even stuffing for your family Thanksgiving turkey every year since 2018. 

With this kind of approach, your readers don’t just learn that you’re obsessed with these two flavors, but also that you’re creative, resourceful, and dedicated to tradition. The key isn’t to explain why these two things must be connected, but rather what you personally seeing this connection reflects about your personality as a whole.

If you’re having a hard time answering that question, take a step back from the actual portmanteau you’ve selected, and think of some of the qualities that make you who you are and aren’t already captured in your common app essay, or UChicago’s first supplement. Maybe it’s your sense of adventure. Maybe it’s your appreciation for melancholy things. Maybe it’s your love of animals. Whatever it is, see if you can use your portmanteau as a spotlight to shine light on this aspect of your personality.

There aren’t any major pitfalls you need to be on the lookout for with this prompt. One slightly subtler thing you ideally want to avoid is creating a portmanteau that reads clunkily. Notice that the real-life examples UChicago gives, and the ones we’ve generated, flow off the tongue. “Socsnow,” on the other hand, unlike “snoccer,” does not.

If you have two things you’re absolutely dying to combine, but can’t think of a sophisticated way to do it linguistically, that’s okay—it’s not a true emergency if the portmanteau reads a little awkwardly, so long as the essay itself is strong. But, since the whole point of the UChicago essays is to test just how creative you can be, ideally you’ll be able to come up with a word that sounds like something people would actually say.

Prompt 2, Option D

A jellyfish is not a fish. cat burglars don’t burgle cats. rhode island is not an island. write an essay about some other misnomer, and either come up with and defend a new name for it or explain why its inaccurate name should be kept. —inspired by sonia chang, class of 2025, and mirabella blair, class of 2027.

While you of course will still ultimately want to connect your misnomer to your own interests and personality, this is a prompt where using introspection to brainstorm may not make the most sense, as it’s possible that you just don’t have an obvious personal connection to anything that has been poorly named.

Instead, think more broadly about your life and the world around you—current events, pop culture, things your friends and family talk about a lot, and so on. Think deeply about the terms you hear thrown around on a daily basis, and if they actually make literal sense. Odds are, you’ll eventually stumble into a word or expression that doesn’t.

For an example you may have thought of before, the NFL season has just started, so maybe you decide to write your essay on the strangeness of calling American football “football” even  though feet are a relatively minor part of the game. For a more unusual example, maybe you notice a container of Gorilla Glue sitting on your counter after a home repair project, and realize that, as far as you know, gorillas are in no way involved in the making of Gorilla Glue.

As you can hopefully see from these examples, and from UChicago’s given above, there are more of these misnomers scattered throughout the language we use every day than you might originally think. That’s why we encourage you to brainstorm by just sitting and thinking about the words you hear often—there’s no need to open the dictionary. Hopefully, you’ll be surprised how many you think of on your own that just don’t make much sense.

While this should still be a personal, reflective essay, the structure may be more similar to your academic essays, since you’re going to be picking a stance (should the inaccurate name be kept or replaced) and defending it. So, like in an academic essay, you might start off by talking about why your misnomer doesn’t make sense, and then focus each of your paragraphs on a different reason why it should be kept or replaced.

However, unlike in an academic essay, the evidence you give for your position should be based on your own life experiences, not on research or a particular scholar’s position on the matter. You don’t want to explain that football players contact the ball with their foot on only 5% of plays, and so the name should be changed, nor do you want to dig up Gorilla Glue’s mission statement to justify why their name is actually a good one.

Rather, your goal is to use your position on this incredibly niche discussion to make broader points about who you are and how you see the world. To do that, you want to connect your ideas about this particular misnomer to formative moments and experiences from your own life.

For example, maybe you argue for the validity of the name Gorilla Glue by discussing your belief that the natural world is more powerful than any human achievement ever could be, a belief which you have developed as a result of numerous camping, backpacking, kayaking, and rock climbing trips throughout your youth.

Alternatively, you could argue against the name by talking about learning English as a second language, and how the challenging process of becoming bilingual taught you the importance of being precise with the words we use. You could then propose a new name, which may be less snappy, but is more literal: The Glue For When Every Other Fails.

If you do argue against replacing the inaccurate name, don’t be afraid to have some fun with your new idea, and even include some humor, along the lines of the suggestion above. Maybe you can also connect your new name to one of your personal experiences, like the time you and your brother accidentally broke a vase and only Gorilla Glue was able to help you stick it back together before your parents got home. If you wrap up your essay with a name that’s too literal, or present that name in a dry, unexciting way, the ending may fall a little flat compared to the rest of your essay.

UChicago already notes this in the prompt, but, along the same lines as a point we made with Option A, don’t write about one of the examples they give. The whole point of these prompts is showcasing your creativity, which you can’t do if you don’t even come up with your own topic.

On a separate note, you generally don’t want to get political in your discussion of the misnomer you pick. For example, maybe you’re inspired to write about how, in contemporary American politics, the term “Republican” does not align with what it used to mean in antiquity. That is a discussion worth having, but not in your college essay. While higher education does lean much further left than society as a whole, you have no way of knowing the political beliefs of your particular admissions officer. So, it’s best to avoid the risk of writing an essay that happens to go directly against one of their core beliefs.

Prompt 2, Option E

Despite their origins in the gupta empire of india or ancient egypt, games like chess or bowling remain widely enjoyed today. what modern game do you believe will withstand the test of time, and why —inspired by adam heiba, class of 2027.

The key to coming up with a strong topic is to define “game” broadly. Chess and bowling have almost nothing in common, other than the element of competition. So, while your mind may immediately go to something popular like football or basketball, we encourage you to spend a little more time brainstorming, to see if you can come up with something more creative.

As a quick aside, however, if a well-known game or sport is one of your true passions, then you should absolutely write your essay about it. If you’re part of six different fantasy football leagues and co-author a football blog with your older brother, don’t overthink this one. Ultimately, genuine passion and excitement is even more important than creativity, as the very best college essays are the ones that sparkle with the student’s enthusiasm.

If nothing immediately comes to mind, though, that’s okay! Refer back to our original advice, of thinking broadly. And, as always, try to think of games that you have some sort of personal connection to, to ensure your essay will be informative and engaging for UChicago admissions officers.

For example, maybe you think back on all the fond memories you have of spending hours playing Monopoly with your neighborhood friends. Or maybe you think about your family’s vacations to the beach every summer, and about cornhole’s consistent presence in the cool early mornings, hot afternoons, and calm evenings around a bonfire. 

Notice that, to repeat our first point, Monopoly and cornhole are completely different activities, so even if your initial reaction to this prompt is “I don’t like board games, though” or “I don’t like sports, though,” don’t rule it out as an option right off the bat (no pun intended).

One last word of advice, which you probably don’t even need at this point for UChicago’s prompts: don’t be afraid to think way outside the box. Maybe you’re one of the founding members of your local beach korfball team. UChicago admissions officers have probably never heard of korfball, which is like basketball but with no dribbling, no backboards, and fully co-ed teams. But they will assuredly love learning about the game, and why you think it will outlast others that are far more popular today.

As we just highlighted at the end of the previous section, remember that this prompt isn’t just “Write about a game.” Rather, your discussion of the game you choose needs to address the question of why you believe it will endure for thousands of years into the future, like chess and bowling. And, as always, although the question is somewhat academic in nature, your response should be grounded in your own personality and experiences, to show your reader what your opinion on this particular topic says about your potential as a UChicago student.

To illustrate the contrast between an “academic” response and the more personal tone you should be shooting for, compare these two potential approaches:

Approach 1: Explaining your belief in the enduring power of Monopoly by discussing how the game’s hundreds of different variations, focusing on everything from Star Wars to mountaineering, have allowed it to attain worldwide popularity and reliability.

Approach 2: Explaining how, although you haven’t played Monopoly with your neighborhood friends in years, the game played a big part in forming a strong foundation for your friendship, which lasts to this day, and you think it will continue to do the same for others far into the future.

Hopefully, the difference here is clear. The first one, while informative, doesn’t teach us anything about your own experiences, beliefs, or overall personality. The second one, on the other hand, shows that you are a loyal friend, have an appreciation for the universality of certain human experiences, and are somewhat nostalgic. Those tangible attributes will allow UChicago admissions officers to get a clear sense of how your values align with theirs, and how you would fit into their campus community more broadly.

Particularly if you fall into the category of someone who immediately has a game you truly love come to mind, make sure you stop for a second and ask yourself if you already wrote your common app essay about that topic. If the answer is yes, unfortunately you’ll need to pick a different game here, as the point of college essays is to teach admissions officers something that isn’t already captured elsewhere in your application. You’re already working with limited space, so don’t voluntarily limit yourself even further by repeating yourself.

Another word of caution is that, if you pick a highly unusual game like korfball, don’t spend too much time explaining the rules. You’re not a coach—you’re an applicant to UChicago. So, you don’t want to spend three paragraphs explaining niche penalties and strategies to avoid drawing them, as that won’t help UChicago admissions officers envision what you’d contribute to their campus community. 

Of course, you do have the freedom to be as creative as you want with your response. So, you could effectively structure your essay around the rules of korfball by, for example, focusing each paragraph on a different rule and connecting the idea behind that rule to an experience from your own life. Ultimately, the only thing that matters is that the essay doesn’t become all about korfball. Like with any college essay, regardless of your topic, ultimately this needs to be an essay about you .

Prompt 2, Option F

There are unwritten rules that everyone follows or has heard at least once in their life. but of course, some rules should be broken or updated. what is an unwritten rule that you wish didn’t exist (our custom is to have five new prompts each year, but this year we decided to break with tradition. enjoy) —inspired by maryam abdella, class of 2026.

This topic may initially seem a little trickier to brainstorm for, since UChicago doesn’t provide you with any concrete examples of the “unwritten rules” they’re talking about. But, along the same lines as much of our advice in the previous “Brainstorming” sections, if you take a step back and let your mind wander a little, you’ll likely find that you’re able to come up with plenty of unwritten rules you find annoying.

A good place to start is thinking back to your childhood. Was there something you often got yelled at for, but didn’t understand why? Maybe you used to put your elbows on the dinner table. Or you never entirely got why your mom was so insistent that your socks had to match.

You can also think about pet peeves you have today, of course. For example, maybe you hate the “driver picks the music” rule, because your music taste is different from everyone else’s in your friend group. Or you could write about a niche unwritten rules imposed by your parents, teachers, coaches, or friends. Maybe your parents insist that the dog eats after you do, but you always feel terrible watching her beg during meals. Or your lacrosse coach won’t let anyone drink Gatorade that’s not one of your school colors.

As you’re probably sick of hearing by now, you also want to make sure that you have a strong enough personal connection to this rule to write a pretty long essay about it. So, as you’re coming up with possibilities, ask yourself why you don’t like this rule. “Because I don’t” won’t make for a very exciting response. 

What will keep admissions officers engaged is a link between your dislike of this rule and your personality, interests, goals for college, and so on. So you’ll want to be sure that link is there before you decide on this prompt as the one you’re responding to.

As always, once you sit down to actually start writing, the key is to make your essay about the link between this unwritten rule and yourself, not about the unwritten rule itself. And, also like with the other prompts, you want to be creative in how you flesh out that link.

For example, in explaining your dislike of your coach’s Gatorade rule, maybe you talk about how your school colors are maroon and gold, but your favorite color is purple, and you love the color so much that it’s become a fundamental aspect of your personality, so it almost physically pains you that you can’t drink purple Gatorade. You could then talk about several of the purple things you love most, and why they’re important to you, like Taylor Swift’s Speak Now , which is your favorite album, the Baltimore Ravens, who are your favorite football team, and Ursula, who is your favorite Disney villain.

Alternatively, you could talk about some of the conversations you’ve had with strangers after they notice your mismatched socks, and how to you, that shows that, while unwritten rules are supposed to enforce some order in a chaotic world, the real foundation of life-human connection—can only be found outside those rules.

Hopefully, these two examples help illustrate that you don’t have to take a “serious” approach to this prompt. As we noted in our breakdown of Option B, writing a more lighthearted response can feel risky, but in reality breaking up the overall formality of your application can be a great way to set yourself apart from other applicants who have taken a more conventional approach. 

That being said, if you’re not confident you’ll be able to make it work, don’t stress. The most important thing with any college essay is that it authentically reflects who you are, and that won’t happen if you’re forcing anything or overextending yourself. Our only point is that, if you do instinctively see an unusual path leading from this prompt, don’t be afraid to take it 🙂

Keep in mind that a college essay is not the same thing as a lunchtime conversation with your friends. So, make sure that, in discussing why this particular unwritten rule irritates you, you don’t accidentally rub someone who doesn’t know you the wrong way.

For example, maybe you think it’s silly that the chef is supposed to serve themselves last, even though they’re the one who cooked the food. This position has merit—you’d likely find plenty of people on the street who agree with you. But if you frame your response around the belief that you should be the first one to enjoy the fruits of your labor, you may come across as callous or even selfish.

Instead, try to structure your opinion around positive traits, ones that UChicago admissions officers will be looking for in their incoming freshman class. For example, you could talk about how you don’t like this unwritten rule because it sets the chef apart from everyone else, which goes against your belief that food and mealtimes should be a place for people to be equal and connect. So, maybe the chef shouldn’t necessarily be served first, but being served last all the time feels counterproductive.

Prompt 2, Option G

And, as always… the classic choose your own adventure option in the spirit of adventurous inquiry, choose one of our past prompts (or create a question of your own). be original, creative, thought provoking. draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world, or future citizen of the university of chicago; take a little risk, and have fun.

Again, this prompt is, on the surface, granting you a lot of leeway. UChicago even ends it with an exclamation point! But you should always remember: they expect a disciplined, thorough, rigorous essay. Don’t let your sense of fun and frolic drown out your serious intellectual ideas.

Pick a prompt that inspires you to write, and connects with your academic interests. If a prompt jumps out at you, and you’re immediately filled with ideas, it’s probably a good fit. Just take it slowly, jot your thoughts down, and get to work. 

Involve your personal connection to that prompt. If you’re not answering any of the 6 prompts UChicago has issued this year, the onus is on you to prove that you and the archival prompt you’ve picked are a match made in heaven. This means having a lot of knowledge and personal investment in your subject matter, and an angle/perspective totally unique to you. 

If making your own question, remember this: YOUR QUESTION IS YOUR HOOK. So make sure it’s not a question that could be found on a standard-issue application, like “When did I overcome a challenge?” or “What’s a place that feels like home?” These prompts are everywhere. They won’t get the job done, and they won’t make an unforgettable first impression. But “Why did I lock myself in the basement and watch The Bee Movie for eighteen hours?” That’s a different story. 

If you look at past UChicago prompts, they tend to be fond of certain things: numbered lists, fairy tales, common phrases, and items of pop culture that can be re-contextualized. They also like hearing your answers to famous questions, and you might have a unique answer to “Et tu, Brute?” or “Do you like pina coladas and getting caught in the rain?” Just remember that the novelty of the question, while the hook of your essay, is not its substance. If your biography and scholarly interests don’t involve pina coladas, or rain, you might just have to pick a different question to answer – as wonderful as that eternal question is.

UChicago essays take a lot of time and thought—but don’t overthink it. The university wants to hear what you have to say, in its full form. That’s why they give you a page limit, and not a word limit—no last minute cutting! Fully develop your ideas in a way that feels natural. If a paragraph needs to be a little thicker, or if you need to include a longer quote from your favorite author, don’t worry about it. These essays can be fun to write and extremely effective.

You can look up lots of examples of essays online, but try not to get intimidated. It’s the nature of the UChicago essays to encourage everyone to showcase their expertise—which is exactly what you should try to do! You may read sample essays and think, “Wow. I’ve never spent a month in Arizona digging up fossils. How can I ever compete?” Try to reframe the essays as a Giant Celebration of everyone’s achievements and interests not a Competition.

If you’ve written your UChicago essay and are looking for feedback, you might want to check out our free peer essay review and paid expert essay review . Since the UChicago essay prompts are weird, it’s important to get an extra set of eyes on them to make sure they are clear and engaging! You can also improve your own writing skills by editing other students’ essays.

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Essay Prompts 2021

The University of Chicago has long been renowned for our provocative essay questions. We think of them as an opportunity for students to tell us about themselves, their tastes, and their ambitions. They can be approached with utter seriousness, complete fancy, or something in between.