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How to Write Successful University of Chicago Essay Supplements

by Will Geiger, on Jul 24, 2021 5:23:15 PM

The University of Chicago or “U Chicago” is a large research university located in the Hyde Park neighborhood of Chicago. It is well-known for quirky essay questions, which should not be surprising, because U Chicago is a very quirky place. We always tell students, “if you have fun with the University of Chicago essays, it is probably a good fit for you” (and if not, maybe another college is a better fit).

Supplemental essays are a very important part of the University of Chicago admissions process. They want to get to know you as a student and learn about what excites you intellectually. On the surface, U Chicago’s essays can seem a little bit daunting, but you can organize all of them with specific moments from your own life experience.

There are two University of Chicago essay supplements, and there is no official word limit to them. Generally, admissions officers need to read applications quite quickly, so brevity is valued. We recommend keeping each response to around 650 words (which is the Common App word limit).

University of Chicago Essay #1:

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.

This essay is essentially a “why this college?” essay question and is meant to identify students who are a great fit for the university. The question is asking you to talk about your fit for U Chicago in both an academic and a non-academic context, so you will want to address both in the essay as specifically as you can.

This question also assumes that you have a strong understanding of the University of Chicago and what makes it unique. As a refresher, you can do some research on their website or think about your past experiences with the university (perhaps you visited campus or spoke with an admissions officer at a college fair). Your goal is to identify 1-2 specific ways the University of Chicago meets your academic, extracurricular, and community needs. You could also show what you will do later as a future graduate of the college. 

Once you figure out your fit, you can connect specific reasons “why U Chicago” to stories from your life. For instance, if you are really interested in getting involved at the University of Chicago’s Institute for Politics, you can relate it back to your experience canvassing for a congressional race in your home district. A moment that is supported by description, dialogue, and details will make the most compelling case for you as a student. Be sure to use Storybuilder to help you turn these stories into a powerful essay.

Next Steps:

  1. Identify specific reasons “why Chicago” meets your academic, extracurricular, community, and “future” needs
  2. Connect these reasons to specific moments
  3. Using Storybuilder build these moments into powerful stories

University of Chicago Essay #2 (choose one prompt)

Essay Option 1:

What if the moon were made of cheese? Or Neptune made of soap? Pick a celestial object, reimagine its material composition, and explore the implications. Feel free to explore the realms of physics, philosophy, fantasy…the sky is the limit!

—Inspired by Tate Flicker, Class of 2025

Essay Option 2

What’s so easy about pie?

—Inspired by Arjun Kalia, Class of 2025

Essay Option 3

In Homer’s Iliad, Helen had a “face that launched a thousand ships.” A millihelen, then, measures the beauty needed to launch one ship. The Sagan unit is used to denote any large quantity (in place of “billions and billions”). A New York Minute measures the period of time between a traffic light turning green and the cab behind you honking. Invent a new unit of measurement. How is it derived? How is it used? What are its equivalents?

—Inspired by Carina Kane, Class of 2024, and Ishaan Goel, Class of 2025

Essay Option 4

"There is no such thing as a new idea" - Mark Twain. Are any pieces of art, literature, philosophy, or technology truly original, or just a different combination of old ideas? Pick something, anything (besides yourself), and explain why it is, or is not, original.

—Inspired by Haina Lu, Class of 2022

Essay Option 5

It's said that history repeats itself. But what about other disciplines? Choose another field (chemistry, philosophy, etc.) and explain how it repeats itself. Explain how it repeats itself.

—Inspired by Ori Brian, AB’19

Essay Option 6

In the spirit of adventurous inquiry (and with the encouragement of one of our current students!) 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!


There is not a one-size-fits-all solution to these essays, because they can go in so many different directions. We have seen a variety of successful essays ranging from creative stories to essays about student research and performance. The purpose of the second U-Chicago supplement is to learn about your intellect, creativity, and view of the world.

Our suggestion for most students is to have fun with this essay and to focus on telling a memorable story.

Next Steps:

  1. Pick a prompt (or choose your own prompt)
  2. Using Storybuilder craft a story that responds to your chosen prompt
  3. Don’t forget about your main Common App or Coalition Application personal statements!

Want to rock your admissions essays and “wow” admissions officers? Our free Storybuilder platform will guide you with simple, step-by-step instructions!

Go back to main Supplemental Essays post.

For more info about college admission and scholarship essays and interviews, sign up for self-paced courses and our award-winning StoryBuilder writing platform FREE at story2.com/college. Want to stay up to date on the latest tips and resources? Follow us @story2 on Instagram!

Will Geiger is co-founder of Scholarships360.org. A graduate of Wake Forest and Penn, Will was previously Senior Assistant Director of Admissions at Kenyon College where he personally reviewed over 10,000 admissions applications and essays and oversaw the merit aid program; Associate Director of College Counseling at a high school in New Haven, Connecticut; and Marketing Manager at Story2.

Topics:college admission

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