Submit your draft for an assessment and hear back within 48 hours!

University of Chicago 2019-20 Supplemental Essay Prompt Guide

Regular Decision: 

University of Chicago 2019-20 Application Essay Question Explanations

The Requirements: 2 essays of 1-2 pages each

Supplemental Essay Type(s): Why, Oddball

This is it, the infamous U Chicago supplemental application. These quirky prompts have been a rite of passage for generations of applicants. So before you dive in, just remember that if they could do it, so can you! Your goal in writing your Chicago extended essay should be the same as ever: to reveal something new to admissions. It might even help to have a few ideas in mind before reading through your options. These prompts are so specific and strange that, in the end, the key is just to follow your instincts. What speaks to you right away? What inspires you?

Respond to the required essay and choose one of the six extended essay options and upload a one- or two-page response.

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.

Think of this run-of-the-mill why essay as the overture to your magnum opus (i.e. the Extended Essay). Chicago wants you to cover all the bases – “learning, community, and future” – so as with any why essay, you’d best buckle down and do your homework. The more specific details you can incorporate into your essay, the more sincere and personal it will feel (and be!). Explore both academic and extracurricular opportunities. How will you pursue your interest in oceanography? With a major in biology and a semester in Australia? What research opportunities will you pursue? Will joining the club crew team help you feel more connected to aquatic life despite your midwest location? One thing you won’t find on the school website, though, is that third piece, that “future” thing. Think about where you’d like to be five or ten years from now – your career or the impact you’d like to have or even just a geographic location. How will a U Chicago education help you get there? How will your scholarly and social pursuits help you grow? Show admissions how U Chicago is the bridge between the person you are and the person you hope to be.

Extended Essay (Choose 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

As you may have heard, the University of Chicago is notorious for its quirky, Oddball questions, and this first question is no exception! As you begin brainstorming for this prompt, remember that these questions are BEGGING for you to have fun with them. So roll up your sleeves, get your creative juices flowing, and start brainstorming!

For this prompt, we suggest that you think about things that possess partial or multiple lives: what does that idea bring up for you? Perhaps, after binge-watching the heroes in Edge of Tomorrow navigate slices of Space-Time, you began composing your own comic book about an arachnid-humanoid species tasked with daring feats of time travel. Maybe, after reading Siddartha over the summer, you became obsessed with the Hindu and Buddhist concept of reincarnation, and began researching cases of hypnotic regression. Whichever direction you choose to go with this, be sure to dig deep as you explain your thought process. After you finish writing, revisit the question again to ensure that you have fully answered it and addressed the “why” part of it. 

Remember, when it comes to all of these extended essay questions, you have OPTIONS! If any of the prompts does not make sense to you or speak to you, just keep going. You only have to choose ONE, so make sure it’s one that allows you to shine!

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

Are Olive Garden’s resources finite or infinite? Can O.G. deliver on their promise of unlimited soup, salad, and breadsticks, or is this just a rote marketing scam to attract more customers? 

There are countless ways to approach this question. Perhaps you want to analyze the question from an economical standpoint, explaining how customers have a finite amount of space in their stomach for soup, salad, or breadsticks just as each Olive Branch can only hold a limited number of customers. Or maybe, having learned about Georg Cantor’s diagonality proof in physics class, you want to argue the case for O.G.’s truly limitless resources. Perhaps your interest in the environment has prompted you to research theories of exhaustible resources that you can easily apply to this question.  Whichever direction you choose to go, make sure that you offer a unique, thoughtful argument backed up by concrete evidence. 

For students who love logic, philosophical debates, proofs, or paradoxes, this is a great question for you! Just remember, you are being given an excellent opportunity to show admissions not only how you reason, but also what subject matters–be it religion, philosophy, economics, or statistics–have shaped how you see the world. So take a stab at this question as you artfully guide admissions through your own unique argument!

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”)

Calling all puzzle makers and wordplay aficionados! What strange, silly questions do you find yourselves wondering about for hours on end? What paradoxes make you giggle to yourself (perhaps the sort that may not have seemed all that useful in your day-to-day life until this very question came along?)

Is a cell phone a drug? Is a sticky note doodle art? Is a sea anemone a plant? Is Cloud Atlas historical fiction? Is chess a sport? Is a thumb a finger? Is the United States a republic? 

This question welcomes playful, witty banter, revealing your capacity to explore categories and contradictions. The University of Chicago is asking you to be original, and show admissions you too can be cleverly inventive in your thinking.

You might start off here by thinking about the various subjects that interest or excite you: Are you passionate about religion, Corn Nuts, the snare drum, geography, nail art, or Comic-Con? How might you use the “But is ___ a _____?” model to allow you to dive deep into one of these subjects?

If an idea grabs you right away, then go ahead, fill in the blanks to craft an awesome riddle that will blow admissions away!

“Fiction reveals truth that reality obscures.” – Jessamyn West
—Inspired by Elizabeth Mansfield, Class of 2020

This question asks you to take a deeper look at the relationship between truth and fiction. As with every Oddball question, you can go in so many different directions with this!

An easy entry point for this question might be to think of a recent novel, film, TV show, or work of art that left you thinking over a new idea, truth, or perspective. Did reading Don Dellilo’s Underworld make you aware of how our current obsession with celebrity has lulled us into a constant state of anxiety? Did watching Get Out haunt you with its nightmarish account of racial hypocrisy in America? 

More than just discussing a work of fiction that influenced you, this question is asking you to examine the very nature of art itself and think about the role that fiction plays in our lives.

Remember, you don’t have to be an aspiring novelist or fiction writer to answer this question. Anyone who loves thinking deeply about art’s relationship to life, and has good examples to back his or her opinions or theories, can truly ace this question!

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

This question ALMOST comes across as serious until the moment you stumble upon the phrase “interplanetary, interstellar, or interdimensional.” At that point, the jig is up, and you see the true nature of this fun, wacky, science-nerd question!

A way to start brainstorming for this prompt is to answer this question: If you could travel anywhere in space or time, where would it be, and why? (If your answer is “Westeros,” you might want to think again for a locale–imaginary or real–that is not quite so popular!)

As with all of these prompts, this question gives you the opportunity to showcase a new passion or area of expertise. Maybe you are obsessed with science fiction, World War II history, astrology, or physics; whatever your interest may be, you can use this question, and your selection of a locale, to explore that area further. Perhaps, taking this in the “interdimensional” direction, you have always been fascinated by Columbus’s epic 1492 voyage and would love to station your campus in the Canary Islands in 1492-1493 so that students could learn about the beliefs, thoughts, and actions of the Native Americans who met Columbus and his crew. 

As you soar off to your fascinating, new UChicago campus, don’t forget to address ALL parts of the prompt, being sure to address the “courses” and “cultural experiences” pieces with creativity  and enthusiasm.

“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!

How lucky you are! Not only to you have prompts 1-5 to choose from, you also have ALL past prompts at your disposal as well as the freedom to invent your own prompt. Remember that all of these questions, as zany as they are, require you to think deeply as you showcase an area of interest or passion that you haven’t previously shown to admissions. Would the historical mash-up question allow you to discuss your passion for Eleanor Roosevelt in a memorable way? Would tackling the portal question give you the opportunity to describe the sci fi graphic novel series you are currently writing? 

So go on, comb through the questions from previous years (and feel free to write your own if you already have an idea brewing!). As soon as you find one that sparks your interest, get ready to wow admissions with your endless curiosity, originality, and passion!

Want more supplemental essay tips and tricks?
Ivy Divider

We thought you might.

Ivy Divider

Contact us for information on rates and more!

Supplemental Essay Prompt Guides:
Share this page:

Want free stuff?

CEA LogoContact us for
rates and more!