Best Ever University of Chicago Application Essay Prompts?

Forget tongue-twisters. University of Chicago likes brain-twisters. Do you?

“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 382 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 Liz@DontSweatTheEssay.com.

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.”

2018-19 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

In 2015, the city of Melbourne, Australia created a “tree-mail” service, in which all of the trees in the city received an email address so that residents could report any tree-related issues. As an unexpected result, people began to email their favorite trees sweet and occasionally humorous letters. Imagine this has been expanded to any object (tree or otherwise) in the world, and share with us the letter you’d send to your favorite.  -Inspired by Hannah Lu, Class of 2020 

Essay Option 2

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?   -Inspired by Chandani Latey, AB’93 

Essay Option 3

The word floccinaucinihilipilification is the act or habit of describing or regarding something as unimportant or of having no value. It originated in the mid-18th century from the Latin words “floccus,” “naucum,” “nihilum,” and “pilus”—all words meaning “of little use.” Coin your own word using parts from any language you choose, tell us its meaning, and describe the plausible (if only to you) scenarios in which it would be most appropriately used.   -Inspired by Ben Zhang, Class of 2022 

Essay Option 4

Lost your keys? Alohomora. Noisy roommate? Quietus. Feel the need to shatter windows for some reason? Finestra. Create your own spell, charm, jinx, or other means for magical mayhem. How is it enacted? Is there an incantation? Does it involve a potion or other magical object? If so, what’s in it or what is it? What does it do?   -Inspired by Emma Sorkin, Class of 2021 

Essay Option 5 

Imagine you’ve struck a deal with the Dean of Admissions himself, Dean Nondorf. It goes as follows: you’re guaranteed admission to the University of Chicago regardless of any circumstances that arise. This bond is grounded on the condition that you’ll obtain a blank, 8.5 x 11 piece of paper, and draw, write, sketch, shade, stencil, paint etc., anything and everything you want on it; your only limitations will be the boundaries of both sides on the single page. Now the catch… your submission, for the rest of your life, will always be the first thing anyone you meet for the first time will see. Whether it’s at a job interview, a blind date, arrival at your first Humanities class, before you even say, “hey,” they’ll already have seen your page, and formulated that first impression. Show us your page. What’s on it, and why? If your piece is largely or exclusively visual, please make sure to share a creator’s accompanying statement of at least 300 words, which we will happily allow to be on its own, separate page.    

PS: This is a creative thought experiment, and selecting this essay prompt does not guarantee your admission to UChicago.  -Inspired by Amandeep Singh Ahluwalia, Class of 2022 

Essay Option 6

In the spirit of adventurous inquiry, pose your own question or choose one of our past prompts. 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.


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