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Getting Quirky with the 2019-20 University of Chicago Essay Prompts


The University of Chicago prides itself on its “Core curriculum” which emphasizes learning across disciplines and teaching students how, rather than what, to think.

Keep those ideals in mind as we examine the University of Chicago essay prompts.

First, we have UChicago’s version of the “Why this school” prompt. (For more general advice on this type of supplement, check out our guide here.


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.

Note: U of C suggests keeping this in the 250-500 word range.


In order to show readers why you belong at UChicago in particular, it’s a good idea to do plenty of research into specific opportunities offered at the school. Let’s look at what kinds of details might work for each area (learning, community, and future).

Learning: Obviously it’s easy to pay lip-service to the famous Core curriculum, so try to dig in and be more specific about what draws you to UChicago’s learning style (even if that ultimately relates back to the Core). For example, if you’re fascinated by the idea of making cities more fair, livable, and sustainable, you might discuss your excitement for the Urban Design Course Cluster; you could mention some cluster courses that interest you and talk about how they will let you explore the topic from multiple angles. Perhaps you hope to take the “Big Problem” course Urban Design with Nature in your third or fourth year.

Community: You could discuss a particular group, organization, or subculture that’s been significant in your life, and how UChicago might provide an environment that’s similar (or perhaps different!).

Future: Give a glimpse of your aspirations post-college—even if you’re 99.9% sure they will change. You just want to show that you have plans and goals and that you’re excited about specific ways UChicago can help you attain them. If your college experience leads you down a different path and into new disciplines—no problem!


Next, you’ll have a choice of six prompts for the “extended essay.” Five of these are new prompts inspired by submissions from UChicago students and alumni; the sixth is a gateway giving you carte blanche to choose a past University of Chicago essay prompt or even create your own. As stated in Essay Option 2 below, the options are indeed endless.

Let’s dig into how to pick a prompt and topic in the face of such a staggering number of possibilities.

Question 2: Extended Essay (Required; Choose one)


Choose one of the six extended essay options and upload a one- or two- page response. We suggest that you aim for around 650 words.


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

Pick this prompt if: the concept of “lives” intrigues you and you can connect it to one of your passions or areas of interest. For example, maybe you’re interested in how people can make art out of “trash”; you could write about how something such as a plastic bottle might have a second “life” as part of a sculpture. You’d also want to show why this idea of a bottle’s second life is so meaningful to you—maybe you’re an artist who cares about reusing raw materials and conserving natural resources.


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

Pick this prompt if: you love to dissect and analyze situations, problems, conundrums, and principles. This is a good opportunity to showcase a particular discipline you’re passionate about, or a perspective or way of thinking that sets you apart—a method to your madness, so to speak! For example, perhaps your extensive research on chaos theory lets you wax eloquently on the mathematical order buried deep within Olive Garden’s salad bar. Or perhaps as a historian, you decide to flip the question on its head and discuss the history of powerful people making promises they can’t possibly keep. Whatever angle you take, be sure to relate it to your own life: explore why this topic engages you, and how these concepts will impact your future.


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”)

Pick this prompt if: well, if these analogies make the slightest bit of sense to you! I’ll readily admit: they were way over my head. When it comes to analogies, I’m as useless as a... a... well, I’m stumped. But if you like logical puzzles, or see some intriguing connection in these examples, or can explain why analogies such as this are personally meaningful to you—or if you’re just crazy for hot dogs and cereal—then have a go at this prompt!


Essay Option 4

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

—Inspired by Elizabeth Mansfield, Class of 2020

Pick this prompt if: your life would feel diminished or empty without the power of stories and storytelling. This prompt beckons to all you aspiring authors out there, and to lovers of literature, drama, film, TV—heck, even Saturday morning cartoons! You’ll want to make your response personal by touching on what this “truth” means to you, how it has been “obscured” in your reality, and how you’ve experienced fiction functioning as a “lie that tells the truth.”


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

Pick this prompt if: you’re into science fiction or fantasy—especially if you love world-building and inter-whatever anthropology/sociology. Ideally, your choice of a “spot” should express something about you as a person, and your discussion of the courses and cultural experiences should tell the reader something about your way of thinking. For example, if you’re an avid chess player, you might pick a planet where the inhabitants do nothing but play chess; your UChicago campus might expose them to other intellectual pursuits, and teach them to apply their checkmating knowledge beyond the chessboard. Note: if, as a new campus site, you propose a black hole—from which not even light can escape, and certainly no undergraduate student—try to put a more positive, less depressing spin on 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!

Pick this prompt if: a past prompt thrills you more than any of this year’s, or if you have some captivating topic on your mind that allows you to shine while wearing the “hats” listed above (writer, thinker, etc.). If you create your own question, make sure the question itself is intriguing and shows something unique about you; make it a question no one else would think to ask.

Here’s our article about last year’s prompts, in case you decide one of those suits you better!


Keep in mind that the approaches above are just suggestions—they aren’t the absolute “right” ways to interpret the prompts. You may have a totally different insight into how to answer one of these creative prompts; if some unique approach inspires you, run with it!

Choose the prompt that most excites you and best lets you demonstrate your unique, eclectic personality and your most creative thinking and writing.

In case you’re not already excited enough to start writing your essay, consider this: if you get accepted, maybe you will craft one of next year’s quirky University of Chicago essay prompts!


Click here for our guide to writing the Common App Essay




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