Best Ever University of Chicago Application Essay Prompts 2022-23

UChicago Wants to Know How You Think

UPDATE! The 2022-23 U Chicago essay prompts are out!

Click right here to read about them.

The following post is from two years ago, but the University of Chicago is so unconventional that you can use a prompt from any year if you wish. Read on and use your imagination:

“You’re on a voyage in the thirteenth century, sailing across the tempestuous seas. What if, suddenly, you fell off the edge of the Earth?”

If you’re applying this fall to the University of Chicago, this is one of the supplemental essay prompts you can choose from. You can also use any prompt from a previous year, including this one, a paragon of pith: “What’s so odd about odd numbers?”

The University of Chicago is famous – or infamous – for their unusual and unusually demanding additional essays. Some of us wait eagerly every year to see what the admissions folks will come up with. The answers are finally here.

Wondering where they get these quirky questions? The answer, on the website, might surprise you: “Each year we email newly admitted and current College students and ask them for essay topics. We receive several hundred responses, many of which are eloquent, intriguing, or downright wacky.”

I work with many students who plan to apply to Chicago before they know about The Essays. When they see the prompts, they have one of two responses: “WOW, this is the place for me.” Or: “Hmmmm. I have nothing to say about any of these.” If you’re in the first category, Chicago might be a good fit for you.

If you’re in the second, take this as useful information about yourself and the University. It may not be the college for you – and that’s absolutely fine. There are dozens of other outstanding choices. Where can you find them? Try The Best 385 Colleges, updated every year, published by Princeton Review.

The supplemental essays are a kind of dialogue between college and applicant. While many of the prompts are straightforward – “Why do you want to attend Our College?” – many others are creative,, personal, and/or intellectually demanding.

For example, the University of Pennsylvania has one supplement, and you can learn a lot about yourself and the university if you sit down to write it: “How will you explore your intellectual and academic interests at the University of Pennsylvania? Please answer this question given the specific undergraduate school to which you are applying. (400-650 words)” If you are a student short on intellectual and academic interests because your focus is marketing or the arts, Penn might not be the right place for you. Again, this is not a criticism of you; it’s valuable information about the kind of students Penn is looking for. If that’s not you, don’t hesitate to move on.

Whether or not you’re planning to apply to Chicago, I bet you’ll find these essay topics fun to read. The infamous essay is one of two additional essays required for Chicago. See below for the second.

If you need help choosing colleges and/or writing your essays – Common App or supplements – shoot me an email at

Here’s the intro on Chicago’s website, followed by this year’s prompts:

“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.”

2022-23 UChicago Supplement

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.

Question 2: Extended Essay (Required; Choose one)

Essay Option 1

Was it a cat I saw? Yo-no-na-ka, ho-ka-ho-ka na-no-yo (Japanese for “the world is a warm place”). Może jutro ta dama da tortu jeżom (Polish for “maybe tomorrow that lady will give a cake to the hedgehogs”). Share a palindrome in any language, and give it a backstory.
– Inspired by Leah Beach, Class of 2026, Lib Gray SB ’12, and Agnes Mazur AB ‘09

Essay Option 2

What advice would a wisdom tooth have?
–Inspired by Melody Dias, Class of 2025

Essay Option 3

You are on an expedition to found a colony on Mars, when from a nearby crater, a group of Martians suddenly emerges. They seem eager to communicate, but they’re the impatient kind and demand you represent the human race in one song, image, memory, proof, or other idea. What do you share with them to show that humanity is worth their time?
—Inspired by Alexander Hastings, Class of 2023, and Olivia Okun-Dubitsky, Class of 2026

Some classic questions from previous years…

Joan of Arkansas. Queen Elizabeth Cady Stanton. Babe Ruth Bader Ginsburg. Mash up a historical figure with a new time period, environment, location, or occupation, and tell us their story.
—Inspired by Drew Donaldson, AB’16

Alice falls down the rabbit hole. Milo drives through the tollbooth. Dorothy is swept up in the tornado. Neo takes the red pill. Don’t tell us about another world you’ve imagined, heard about, or created. Rather, tell us about its portal. Sure, some people think of the University of Chicago as a portal to their future, but please choose another portal to write about.
—Inspired by Raphael Hallerman, Class of 2020

What’s so odd about odd numbers?
—Inspired by Mario Rosasco, AB’09

Vestigiality refers to genetically determined structures or attributes that have apparently lost most or all of their ancestral function, but have been retained during the process of evolution. In humans, for instance, the appendix is thought to be a vestigial structure. Describe something vestigial (real or imagined) and provide an explanation for its existence.
—Inspired by Tiffany Kim, Class of 2020

The University of Chicago Essay Prompts Page is RIGHT HERE

If you’d like help drafting these essays or any others, please contact me: