Updated August 10, 2026
How to Write the University of Chicago Supplemental Essays for 2026-2027
Bonus Material: PrepMaven’s 50+ Real Supplemental Essays for Ivy+ Schools
Expert guidance provided by Mike Kleynman (PhD in English, 10+ years’ experience coaching admissions) and reviewed by Kevin Wong (co-founder PrepMaven, 20+ years’ experience coaching admissions).
Last year, the University of Chicago admitted under 5% of applicants, which means that if University of Chicago is your dream school, your application needs to be unbelievably impressive!
If you know anything about applying to University of Chicago, you may already know that they’re famous (or infamous) for having very atypical supplemental essays–in fact, they pride themselves on the weirdness of their prompts!
Fortunately, at PrepMaven, we’ve helped thousands of students craft compelling college application essays. We’ve also summarized that expertise in our Ultimate Guide to College Supplemental Essays.
It doesn’t hurt that many of our expert tutors have been admitted to elite schools like Princeton, University of Chicago, and Harvard themselves, and so they know exactly what works.
In this guide, we’ll break down how to write the University of Chicago supplemental essays for the upcoming admissions cycle, explaining how to maximize your chances of acceptance.
As you read on, check out our free resource linked below: it contains real, successful examples of supplemental essays written for Ivies and other top schools–including a real essay that got a student admitted into University of Chicago!
Jump to section:
University of Chicago’s 2026-2027 Essay Prompts
How to Write University of Chicago’s First Essay: “Why Us?”
How to Write University of Chicago’s Second Essay
Real University of Chicago Supplemental Essay Analysis
Next steps
University of Chicago’s 2026-2027 Essay Prompts
For this admissions cycle, University of Chicago has 2 required supplemental essays.
The first essay gives you the following 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.
That’s a classic “Why us?” supplemental essay prompt, one you’ll see many times through your college application process.
While University of Chicago does not have a word limit on their essays, they recommend 300-600 words for this first essay.
In fact, if you’re writing according to our guidelines for the “Why us” essay type, you’ll probably already have a template that you can use to save yourself lots of work on this essay.
Alas, that’s not the case for University of Chicago’s second supplemental, which is both longer and weirder. Here, you’ll have to choose one of six options:
Essay Option 1
Food for thought: How do thoughts eat?
– Inspired by Ernest Leong, Class of 2026.
Essay Option 2
The James Webb Space Telescope, launched in 2021, utilized origami-inspired techniques to compactly store and deploy its sunshield in space. Choose an artistic practice and use its principles to propose an elegant solution to a problem.
-Inspired by Akhil Korra, Class of 2028
Essay Option 3
Sometimes metaphors get mixed up. For one reason or another, one could say, “we’ll burn that bridge when we get there” or “the world is your china shop”. Make up your own mixed metaphor. Explain how it could make sense, be understood, or even applied.
-Inspired by Julia Nieberg, Class of 2029
Essay Option 4
The Olympics have long celebrated the pinnacle of human athletic achievement. But what if they expanded to honor the mundane? Imagine a new Olympic event built around an everyday activity like speed dishwashing or competitive grocery bagging. How is it scored, officiated, and judged? Why is it a worthy addition?
-Inspired by Ewan Smith, Class of 2028
Essay Option 5
AI: Allen Iverson. NASA, or the North American Saxophone Alliance. Share a potentially confounding, comedic, or captivating example of MIA (Mistaken Identity of Acronym) and tell us its backstory.
-Inspired by Jeeho Byun, Class of 2030
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!
As you can tell, there’s no standard way to approach these essays… You’re going to have to set aside the time to craft a new, original essay in response to one of these prompts.
As with the first essay, there’s no strict word limit: instead, University of Chicago’s FAQ page suggests between 500 and 700 words. That means this essay will likely be about as long as your Common App personal statement!
Read on for guidance about how to tackle the University of Chicago supplemental essays, and download the 50+ Real Sample Essays That Worked below for inspiration!
How to Write University of Chicago’s First Essay: “Why Us?”
The first supplemental essay prompt from University of Chicago is a classic essay type that we’ve written a lot about in our guide to the “Why this College?” essay.
The analogy we like to use is that you can approach this essay a bit like a first date: you want to show why the two of you (you and the college) are a good match.
A lot of students just start by talking about how great the school they’re applying to is, but that’s the wrong move. University of Chicago already knows it’s hot stuff (they rejected over 90% of applicants, remember?).
What they want to know is why you are such a good fit for their offerings and culture, and vice versa.
So, we recommend tackling this essay in three steps:
- Step 1: Research unique offerings
This first step is key. Research what University of Chicago offers that other universities do not.
This could be a lot of things:
- Specific research lab
- A professor whose class you want to take
- Rare majors/minors/concentrations/courses
- Unique work or service programs
- A particular curriculum design that speaks to your interests
With all of these, the key is uniqueness. Pick things that really set University of Chicago apart, so they know you’re serious about attending.
- Step 2: Link to your story
People usually do step 1, but many forget to do this second step. It’s not enough to show that you did your research into University of Chicago’s offerings.
You need to show that these offerings actually speak to your interests, capabilities, and goals.
So, for every specific aspect of University of Chicago you mention, you need to connect it back to something you’ve already done or some existing passion of yours.
Quality over quantity is the rule here. Instead of listing 5 specific programs at University of Chicago you like, list 2, but go on to explain how each one speaks to the experiences you’ve already had or the goals you’ve set for yourself.
- Step 3: Create a frame for your essay
Because this essay is as much about you as it is about University of Chicago, you can create an introduction and conclusion (a “frame”) that you tweak only slightly for multiple schools.
The first paragraph, whenever possible, should be eye-catching and specific to you. Tell a story or anecdote that sets the stage for what your interests/goals are!
Are you going to apply to these schools as a Math major? Well, then you might want to start the essays with a short description of the moment you fell in love with math, or with what burning questions drive you to pursue it in college.
Then, dive into all those good University of Chicago specifics you’ve been researching, connecting them back to your own life.
Finally, use a conclusion that ties back to your introduction. Keep it really short, but keep it about you! Great ideas here would be to talk about how the college will serve your long term goals, or how you hope to contribute to its community.
The good news is you can easily reuse the frame anytime a school asks “why us?”
We’ll cover the second, harder, University of Chicago supplemental below. In the meantime, download our collection of over 50 real supplemental essays below, which also include many examples of the “Why this school?” essay!
How to Write University of Chicago’s Second Essay
As you can tell by the prompts, this essay is really a wildcard one–often the hardest kind of college supplemental essay to write!
Our advice? Take risks, get creative, and treat this as an opportunity to tell an extended story.
Our best advice on your Common App personal statement is, first and foremost, to tell a story.
The same holds true for this University of Chicago supplemental, and that’s how you should decide which University of Chicago supplemental prompt to pick.
We can’t stress that latter point enough: first, come up with an interesting anecdote from your life that hasn’t been showcased elsewhere in your college application.
Then, pick the UChicago essay prompt that allows you to tell the anecdote.
At the end of the day, admissions officers don’t care what prompt you choose. They’ll only care about how interesting the final result is. So, pick a story first, then pick a prompt.
Once you’ve got the right story, what does it need to do to impress college admissions officers?
We’ve got another post dedicated to the Qualities of a Successful College Essay where we explore this question in depth.
Specifically for UChicago, here’s what you want to do:
- Make sure your essay is introspective
Whatever story you tell, be sure that it shows you thinking critically about your life and your place in the world.
Introspective just means that as University of Chicago admissions officers read your essay, they can see you engaging in a process of self-reflection, considering your experiences, values, and goals.
- Use your own voice
A big problem in college essays, whether supplemental essays or personal statements, is that many students try to sound like someone they’re not.
To put it bluntly: don’t treat this like an essay for school. Don’t get out the thesaurus, don’t start throwing around words like “plethora” and “nevertheless.”
Read your University of Chicago supplemental aloud: does it sound like you? If not, it’s time to edit it.
We know this can sound vague, but you can see great examples of what we mean by “voice” in the sample University of Chicago essay below, and in our collection of over 50 Supplemental Essays that Worked for schools like Princeton, Harvard, and University of Chicago !
- Be honest
Vulnerability can work wonders in this essay. University of Chicago has made it very clear that they’re interested in risk-takers, and this supplemental essay is your best chance to show it.
Instead of writing what you think they want to hear, write the truth, even if it’s uncomfortable. Sometimes, admitting something about yourself that might not put you in the best light can actually be a strong, advantageous move in college admissions.
Of course, it’s a big risk: we recommend working with a trusted college essay expert to make sure you’re not being a little too honest.
- Don’t be generic or cliche
Nothing sinks an essay faster than it being boring or cliche. That’s especially true for University of Chicago, where the prompt is designed to help you avoid those things.
If you’re writing a sentence that 1000 other students could have written, that’s a problem–because odds are, they already have. And, odds are, University of Chicago admissions officers have had to read a lot of them.
Rule number 4 can be rephrased more bluntly: don’t be boring.
For an example of an essay that does all these things (and more), read on below for a recent example of a University of Chicago supplemental that got its writer an acceptance letter!
Real University of Chicago Supplemental Essay Analysis
Below, we’ll give you a supplemental essay written by one of our tutors that earned them admission into University of Chicago recently!
We’ll then offer a short breakdown of what allows it to work. Here’s the essay:
Prompt: Dog and Cat. Coffee and Tea. Great Gatsby and Catcher in the Rye. Everyone knows there are two types of people in the world. What are they?
There are two types of people in the world.
The first type of person opened University of Chicago’s list of essays and found one that spoke to them. Maybe they knew exactly which vestigial structure they would defend or spell they would create. Regardless, they never had any trouble selecting a prompt; they picked one and ran with it.
And then, there’s my group, the ones who no matter how many times they reread the list, couldn’t pick a single topic. The ones who simultaneously wanted to divide by zero, find X, or compare apples to oranges. The ones who were fascinated by the questions themselves, for whom pondering each question in turn was more interesting than attempting to come to a conclusion about any one of them. The fact is, my group is right. A well-crafted question is so much more than a single essay; it deserves to be a back-and-forth that lasts a min-finity (noun: a very long period of time that seems to pass in a minute due to enjoyment).
First, I thought I’d write about what’s not easy about pie. I detailed how each Thanksgiving my Dad makes five pies from scratch, using his grandmother’s rolling pin and a crust recipe based on the latest culinary science. I talked about the hip-hop that filled my kitchen, the chimes of measuring spoons, and the occasional whir of an ancient Cuisinart. I wanted to explain why my Dad’s approach to life – that if something is worth doing, it’s worth doing right—means he won’t eat Dunkin’ Donuts. To me, doing college right entails heated classroom debates over the ethics of gene-editing—the best of which spill over into dinner and late nights—not just partying with my two hundred best friends.
Then, I wanted to explain how math, like history, repeats itself. In my math classes, I’ve spent hours hunched over my desk, furiously proving obscure conjectures. Once I can say ‘Quod Erat Demonstrandum’, I sit up and relish my success for a moment before realizing a more elegant approach exists. Dissatisfied, I reassume my hunched posture and grasp my pencil in pursuit of elegance. This cycle of discovery and discontent continues until my pencil is a stub, my wrists ache, and I realize an hour has passed. I wanted to explain how works of mathematics cannot be truly complete, as more elegant solutions always exist.
But then, I thought of my favorite portal. The white wooden fence wards off the outside world and the giant statue of Paul Bunyan looks down on the lucky few who enter Camp Nebagamon. A sign reading “This Shall Be a Place of Welcome For All” in countless languages hangs at the entrance, affirming acceptance. When boys pass through this gate, they are able to disentangle themselves from technology and the stresses of real-life and truly be a kid. Passing through this portal transformed me into the best version of myself. I wanted to help others see its magic.
The list of potential questions includes just about each one on that list. I explored what a mantis shrimp sees, what makes odd numbers odd, or what a picture wants. Each prompt was an opportunity to highlight a different aspect of my character and explore different ideas. My trouble came in picking which to unpack. I wouldn’t be myself without all of them, and I wouldn’t want to surround myself with people for whom the choice is obvious. More: questions like these shouldn’t be answered by a single person, but as part of an ongoing dialogue between people of different minds. Even then a definitive answer may not be reached. And while some may claim that a 650-word response is more than enough to ‘destroy a question’, in the words of University of Chicago’s famous president Robert Hutchins, “Frankly, my dear, I don’t give a damn.”
So, why does this essay work? Let’s do a quick breakdown:
- Clever, unique opening
While the “meta” essay has become overused and cliche, it works for this essay because it addresses the nature of the prompt (“there are two kinds of people”) in an usual, deliberate way.
It’s not being meta for the sake of being meta: it’s trying to say something about the writer by exploring their experience with this specific prompt.
Our college essay tutors can help you craft your own clever essay openings for UChicago!
- Voice!
If you read this aloud, it’s clear that you’re reading the writing of one particular person. In other words, it doesn’t sound like someone who’s trying to sound like a “writer.”
It sounds like a real human! All of the small elements–the contractions, the short, experimental sentences, the jokes–come together to make it feel like someone is talking to us.
Trust me, if you’d been reading thousands of application essays, you’d be grateful to the one that actually felt more like a story or a conversation.
- It’s introspective
The whole essay is really the student’s thought process, as they evaluate what they want to write about.
But what’s important is that this thought process allows the writer to explore the core aspects of who they are, from their values to their dreams.
The student brings up not only their interests in gene editing and mathematics, but also mentions how they hope to “help others see the magic” of accepting, stress-free places.
- It’s not generic
Nobody else could have written this essay, period. Why? Because of the level of specific detail!
From anecdotes about family members to experiences in math classes to hyper specific questions like “what a mantis shrimp sees,” this essay overflows with the particularities of the writer’s perspective.
That goes a long way: if your essay is boring or sounds like a hundred other essays, it’s already dead in the water. The admissions officers at University of Chicago will forget about it (and you!) before they’re even finished reading it.
But an essay like this one sticks with the reader. Whatever their feelings about it, they’re not likely to forget the student who wrote it.
Below, find over 50 other memorable, unique supplementals that got students accepted into elite schools like Ivies. There’s no better resource to use as you start your own University of Chicago supplemental essays!
Next Steps
Once you’re ready to start writing supplemental essays for University of Chicago and your other schools, we have two main pieces of advice.
First: read real, successful sample supplemental essays that helped get students into elite schools like University of Chicago.
Most people don’t really know what schools like UChicago actually want from the supplemental essays, and the best solution is to spend lots of time reviewing sample essays. We’ve collected over 50 of these essays in the free resource below.
Second: get expert help. Whether you’re a brilliant writer or just an okay one, you’ll benefit tremendously from the advice of someone who’s already successfully navigated the high-stakes college application process.
Unfortunately, not all college essay tutors are created equal: picking the right one can be the difference between getting into your dream school or just wasting your money.
That’s why we had our experts come up with the definitive ranking of the 14 Best College Essay Services, evaluating everything from tutor credentials to customer reviews. Check out that list, and make sure you only work with the best.
And when you’re ready to work with our team of college essay experts–who earned admission to elite schools like Princeton and University of Chicago before undergoing a rigorous training process–contact us to get matched with a tutor!
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Mike Kleynman is an expert test prep tutor (SAT/ACT/LSAT) and college essay consultant, with over a decade of experience and industry-leading results.
With average final scores of 34+ on the ACT and 1500+ on the SAT, nearly all of Mike’s test prep students score in the top percentiles. They also routinely earn admission to the most selective universities: just last year, Mike had students accepted to Brown, Dartmouth, MIT, UC Berkeley, USC, and Carnegie Mellon. The average final LSAT score of his students is over 172, and his law school application coaching students have been accepted to Harvard, Yale, and Columbia Law.
Mike holds a PhD in English from Duke University.