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 accepted 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 2024/2025 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 2024/2025 school year.
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
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
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
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
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.
Question 1: Why UChicago?
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
Question 2: Extended Essay
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.
What Do They Want to See in Your 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 story
- 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!
Potential Topics to Write About
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
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.
You can let your imagination run wild with this prompt. Think of an expression that includes a color that isn't one of those mentioned in the prompt. Spend some time on this! For this prompt, UChicago wants to see how imaginative you can be, but the most important part of this essay is justifying what your new expression means and why it matters.
Make your response as wacky and original as you like, but remember to tie it back to yourself and your interests. For instance, instead of "seeing red" you could change the expression to "seeing lavender." This could mean, instead of the anger that accompanies seeing red, seeing lavender is when you're purposefully calm and thoughtful about things.
For example, you might be "seeing lavender" whenever you do your daily meditation, or go for a nature walk, or get into a flow state when painting, coding, or working through geometric proofs. Weaving your story into your essay will show UChicago that you’re creative and intellectually curious, two characteristics they love to see in applicants.
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?
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.") If you choose to answer this question literally, you could discuss having a greater appreciation for simple pleasures than you did when you were younger. For example, that you eat ice cream for breakfast more now than you ever did as a kid because there's no one to stop you. Be sure to use specific examples and tie them back to who you are as a person and what your values are.
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.
A less literal interpretation could discuss how, as we get older, we build a time capsule inside ourselves full of memories that we can visit at any time which allows us to return to whatever age we like.
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
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?
There are a lot of ways to tackle this prompt. All you need to do is choose a group and discuss which of its members doesn't fit in. Again, spend some time deciding on an option you can write thoughtfully about. Are you a movie buff who hates The Godfather Part III? A Harry Potter fan who has never understood why Slytherin still exists? Maybe you've just never understood why boredom is considered as bad as the other deadly sins?
What U Chicago is looking for here is your creativity as well as your interests/values. If you chose The Godfather movies as your grouping, you could discuss how important good writing is to you and how The Godfather Part III didn't match the heights achieved by its two predecessors. You could then tie that into being, say, a future English major and how effective writing has impacted your life and your career decisions.
If you chose to discuss why boredom shouldn't be considered one of the seven deadly sins, you could discuss times being bored have helped you achieve breakthroughs in life: maybe they taught you how to create your own fun, or reflect on your future.
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.”
This is a classic off-the-wall UChicago prompt. If you choose to answer it, you'll give your best defense to a slang word or phrase that's no longer in style. An interesting aspect is that the slang can be in any language. So if you strongly feel that the French need to bring back saying "Zut alors!" this is your chance to make your case.
As with the other prompts, the specific slang you choose doesn't matter (as long as it's not offensive); it's your explanation of why it's meaningful to you. For such a quirky prompt like this, it's easy to get carried away with humor or cleverness and make an argument that's very interesting but doesn't actually give UChicago insight about yourself. By all means, choose any obscure slang you'd like, but make sure that, when you describe why you like it, that you're giving insight into your personality, interests, experiences, and/or values.
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 prompt is your chance to be more overtly academic in your response. In choosing and working through a Fermi estimation problem, you’ll be able to show your interest in any topic like history, art, economics, science, etc.
Coming up with an accurate estimate may seem like the most intimidating part of the prompt, but it's actually the least important part. UChicago is much more interested in how you came up with your estimate than how accurate it is. That means you'll need to explain your train of thought clearly and thoroughly.
For example, say you decide to estimate how many drops of rain fall on Lake Michigan each year. A logical first step would be learning the surface area of Lake Michigan. You'd then need to find the annual rainfall in the area. After that, you'd calculate the volume of rainfall that actually falls on the lake, such as by multiplying the lake's surface area by the rainfall depth. You'd then need to convert that value to drops of water, and you'd have your answer.
UChicago wants to see your logic and reasoning skills here, so break the problem down into as many steps as you need and clearly explain how any why you completed each step.
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.
Topics to Avoid
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.
Question 1
Dear University of Chicago,
It fills me up with that gooey sap you feel late at night when I think about things that are really special to me about you. Sometimes I just hunger for more, but I keep that a secret. The mail you send is such a tease; I like to imagine additional words on the page. Words like "you're accepted" or "you're awesome!" or "don't worry, she still loves you!" but I know they're all lies. You never called after that one time, I visited you thrice, but you never come around anymore. Tell me, was I just one in a line of many? Was I just another supple "applicant" to you, looking for a place to live, looking for someone to teach me the ways of the world? The closeness between us was beautiful, it couldn't have been just me that felt it, I know you felt it too. The intimacy was akin to that of scholar and original text, your depth as a person is astounding! To be honest, I must confess I had already dreamt of a rosy future together, one filled with late nights and long discussions over the Gothic era and the ethical stage of Kierkegaard, we would watch the sunset together and spend every Christmas snuggled in blankets. Eventually we would get older, I would become a well-educated corporate lawyer and you would enrich yourself within the domain of human knowledge. Your cup overfloweth with academic genius, pour a little on me. You're legendary for it, they all told me it would never work out between us, but I had hope. I had so much hope; I replied to your adorable letters and put up with your puns. I knew going into it that you would be an expensive one to keep around, I accounted for all that; I understand someone of your caliber and taste.
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.'
Always,
Rohan
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.
Question 2
This essay is from several years ago, so it doesn't use a current prompt, but it's still helpful to read and analyze.
Here's the prompt:
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.
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."
