Expert guidance for all your college essays

Prompt’s Essay Specialists share tips to help you write better essays in less time

Get fresh essay tips in your inbox

All Posts

How to Answer the University of Chicago Essay Prompts 2018-19


All University of Chicago applicants will answer the same “Why UChicago” prompt ; however, for the “extended essay” you’ll have a choice of six rather...well, “weird” prompts, one of which opens the door to an archive of past prompts and even invites you to create your own. With literally limitless possibilities, how do you choose which University of Chicago essay prompt to answer and what to write about?

The good news is, each prompt will allow you to express something unique about yourself and how you see the world. Let’s explore the six (+infinity) options.


Choose one of the six extended essay options and upload a one- or two- page response. Most applicants write approximately 500 words.


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

Pick this prompt if: you can think of an object that represents an important aspect of your life. It could be a possession of yours: your personal ping-pong paddle, or your hiking backpack. Or it could be something you don’t own but that embodies a passion of yours: El Capitan, for example.


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

Pick this prompt if: you’re a history, sci-fi, or fantasy buff, and love to imagine life in other eras or worlds, or if you like to ponder philosophical or scientific questions. This prompt could suit storytellers who yearn to tell a good adventure yarn, or philosophers who like to conduct thought experiments.


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

Pick this prompt if: you speak multiple languages and sometimes fuse them together, or if you just love etymology. To make this essay compelling, it’s a good idea to make your hypothetical scenarios relevant to your life.


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

Obviously Harry Potter fans might use their flying broomsticks to brush aside the other prompt options here. Similar to the previous prompt, you’ll want to tie your spell/hex/curse to specific details of your life and make its power something relevant to your goals and passions.

  • (Pro-witch/wizard-tip: You don’t have to save the world with your spell, but try not to be too evil, either!)


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

Pick this prompt if: you express yourself as much visually as through words, or if you tend to think in vivid images. What images represent the best and most unique parts of you? For example, a peace sign alone might be rather generic, but perhaps you could surround it with specific passions in your own life related to your commitment to peace.

  • Tip: Since you’re allowed to use both sides of the page, perhaps you could convey two sides of yourself and how they fit together!

Whether your response is primarily visual or not, you’ll also want to write about the significance of these images to your life.


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. Last year's prompts can be found here.

Pick this prompt if: none of the other prompts grab you, a past prompt calls out to you, or you have some burning question constantly on your mind.

  • If you pose your own question, make it fun, surprising, and specific enough so that the question itself expresses something essential about who you are.


The best University of Chicago essay prompt for you is the one that most inspires you and lets you showcase your personality, creative thinking, and energetic writing (or sketching!). These zany University of Chicago essay prompts give you the opportunity to show that wild, quirky side of yourself that might not come through in other areas of your application.


Need help with your common app essay? Sign up to get our free guided brainstorming tools!

Prompt’s Essay Specialists reviewed 13,000 admissions essays in 2018, helping thousands of students submit their applications with confidence.

Get Your Essay Reviewed

Related Posts

How to Write Strong UPenn Essays 2020-21: Why UPenn and Community

Admissions readers want to understand why the college you’re applying to is a good fit for you. This guid...
Lauren Oct 19, 2020 11:48:05 AM

How to Write Admission-Worthy UT Austin Essays

Good news! The UT Austin essay prompts remain simple and flexible — overall, they're an excellent chance ...
Reina Oct 19, 2020 11:07:48 AM

How to Write the UNC Essays for 2020-21

The University of North Carolina at Chapel Hill doesn’t use admissions interviews, so these short answer ...
Nick Oct 19, 2020 10:15:19 AM