How To Write The University of Chicago Supplemental Essays (2019-2020)



Welcome to the supplemental essays for the University of Chicago! These are a doozy. I'll be frank with you: I can only take you so far with these in a blog post, but I will do my best to spark your imagination. As always, UChicago has done a terrific job asking questions that require serious soul-searching—even if these questions are about such things as the difference between cereal and soup. Look at these prompts as an opportunity to get to know yourself, and write some weird essays.

But first, a typical essay prompt.

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.


This is a fairly standard “Why here?” question. As you know, it’s important that you be very specific about your desire to attend the colleges on your list. There’s no recycling an essay you wrote for somewhere else. This one needs to be all about how your “wishes” fit with the opportunities available at UChicago.


Your task here is to show UChicago that:


  1. You know what you want to study (make a major up if you’re actually undecided—just choose what makes most sense based on your past experiences);

  2. You can talk about some upper-level classes you’d like to take a UChicago (in line with your academic direction. Don’t mention anything that’s readily available at other universities—pick something interesting and unusual);

  3. You can mention a few professors you’d be interested in working with (again, who teach in a subject related to your academic path. These should be tenured professors, or at least professors you know will be there for the next four years. Not sure how the vicious academic hierarchy works? Ask us);

  4. You have a sense of which extracurricular clubs you’d like to be a part of (do your research—the clubs you choose to discuss should be a logical extension of your past academic and extracurricular achievements.)

  5. You have identified any other academic or extracurricular opportunities that UChicago and the area will provide you with.

Again, this essay isn’t just about UChicago. It’s also about you. Make sure you’re relating what you want to do at UChicago to your past experiences—that the professors and courses that interest you will help you build on your most impressive achievements.


Question 2: Extended Essay (Required; Choose one)


Let me preface my discussion of these different questions with a few remarks. Every year, UChicago does a fabulous job at providing its applicants with remarkably creative prompts. One of the effects of their selection of quirky questions is that it is extremely difficult to provide general guidance on how to respond. In other words, they’ve done a great job ensuring that your responses must be authentic and spontaneous. My number one recommendation here is to approach these like puzzles. Give them some thought. But, if nothing occurs to you after a few minutes of meditation, move onto the next question. Do not force any one prompt.


Essay Option 1

Cats have nine lives, Pac-Man has 3 lives, and radioactive isotopes have half-lives. How many lives does something else—conceptual or actual—have, and why?

—Inspired by Kedrick Shin, Class of 2019


Even if I had a great idea for a response to this question, I wouldn’t tell you what it was, because it wouldn’t help you. As I said above, these questions are like puzzles, except the response, when you find it, may (and should, in fact) only make sense to you until you explain it.


Essay Option 2

If there’s a limited amount of matter in the universe, how can Olive Garden (along with other restaurants and their concepts of food infinity) offer truly unlimited soup, salad, and breadsticks? Explain this using any method of analysis you wish—physics, biology, economics, history, theology… the options, as you can tell, are endless.

—Inspired by Yoonseo Lee, Class of 2023


Again, sit with this one for a bit. Does some original methodology for proving infinity, unlimitedness, or endlessness occur to you? To me the question seems a bit silly, but I’ve never been a big fan of Olive Garden. My personal feeling is that the restaurant can reasonably offer unlimited soup, salad, and breadsticks because who could possible eat an unlimited amount of second-rate sides and appetizers. Or anything, for that matter. But maybe you have a more original and essay-worthy take.


Essay Option 3

A hot dog might be a sandwich, and cereal might be a soup, but is a ______ a ______?

—Inspired by Arya Muralidharan, Class of 2021 (and dozens of others who, this year and in past years, have submitted the question “Is a hot dog a sandwich,” to which we reply, “maybe”)


This was a big debate on Twitter, right? All I can do is repeat that, after sitting with this for a bit, you either will, or will not find something clever to write about. The obvious point of this question would, it seems, be that the answer can only be “maybe,” as UChicago itself says. So maybe you have a response that emphasizes subjectivity, relativity, or what-have-you. Your question isn’t nearly as important as what you do with it. I wonder, for example, if Alexa is a piece of furniture. I saw a child the other day being Instagrammed with its mother, noticed that the two were dressed the same, and wondered: are babies fashion accessories? But, of course, this isn’t really a yes or no question. It’s about what you do with your comparison, and what it ends up saying about you and your core values and passions.


Essay Option 4

“Fiction reveals truth that reality obscures.” – Jessamyn West

—Inspired by Elizabeth Mansfield, Class of 2020


One of my own personal favorite thinkers said that “Truth has the structure of a fiction.” I love this question. You may not. These UChicago prompts tickle us all differently. All I’ll say is: lots of people have meaningful things to write about family legends, neighborhood myths, and of course, the poems, plays, and novels we identify with. If you’re tickled by this prompt, go for it—it’s a great chance to share a story which, even if it’s not “real,” holds personal meaning.


Essay Option 5

UChicago has international campus centers around the world, but we don’t have any interplanetary, interstellar, or interdimensional campuses… yet! Propose a spot in time or space, in this or any universe, for a new UChicago campus. What types of courses would be taught at this site? What cultural experiences await students who study there?

—Inspired by Peter Jasperse, Class of 2022


Not a fan, but if, for example, you believe in life on Mars—and that Martians need a UChicago-style education—go for it!


Essay Option 6

“Don’t be afraid to pick past prompts! I liked some of the ones from previous years more than those made newly available for my year. Also, don’t worry about the ‘correct’ way to interpret a question. If there exists a correct way to interpret the prompt I chose, it certainly was not my answer.”

—Matthew Lohrs, Class of 2023


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!


Now, obviously this all boils down to, “Write whatever you like.” The Common App does this with their final prompt. Harvard does this with their “optional” supplemental essay. You’ll sometimes catch a break and be given the option to “write whatever you like.” Notice, however, that UChicago, as always, does something a little different. You can choose one of the many past prompts or “create a question of your own.” If you choose the latter route, actually write out your question. And believe me when I say it had better be as inventive as the ones that UChicago proposes.


As always, we're here to help. Don't hesitate to reach out.

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*Results are based on students whom H&C Education worked with in a comprehensive fashion before and during the formation of H&C Education. Prior results do not guarantee a similar outcome.

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