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University of Chicago 2020-21 Supplemental Essay Prompt Guide

University of Chicago 2020-21 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)

Essay Option 1
Who does Sally sell her seashells to? How much wood can a woodchuck really chuck if a woodchuck could chuck wood? Pick a favorite tongue twister (either originally in English or translated from another language) and consider a resolution to its conundrum using the method of your choice. Math, philosophy, linguistics… it’s all up to you (or your woodchuck).
—Inspired by Blessing Nnate, Class of 2024

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!

This prompt is calling to all puzzle lovers and wordplay aficionados. What tongue-twisters were your favorite to try to master as a child? And once you had them down pat, did you ever stop to think about what you were really saying? Who is Sally after all, and what was the point of collecting all those seashells? This question welcomes playful twists and witty ideas, revealing your capacity to tell stories and show off your imagination. The University of Chicago is asking you to be original, and show that you can be cleverly inventive in your thinking.

After you choose a tongue twister, you might start off here by thinking about the various subjects that interest or excite you, or even your own past experiences: Maybe Peter Piper picked a peck of pickled peppers because, like you, he’s the oldest of three siblings, and always helped his parents make sure his younger brothers and sisters ate enough vegetables every week. If an idea grabs you right away, then go ahead and fill in the blanks to craft that winning answer!


Essay Option 2
What can actually be divided by zero?
—Inspired by Mai Vu, Class of 2024

There are countless ways to approach this question, and our first tip to you is this: Don’t get lost in the technical aspect of your answer. If you’re seriously into mathematics and can actually discuss this in a purely academic way while still keeping the tone of your essay approachable, then go for it. However, just like with every essay prompt, there is no “correct” answer here — if you want to stretch your creative wings, a question about math can still be the place to do it.

Perhaps you’d like to answer this question with a real-life experience, like a time where you experienced the grief that comes with the death of a pet or a loved one. At that point in time, did you feel like your emotions were so difficult to put into words that you could only relate the feeling of trying to divide by zero? Or maybe you’d like to take this prompt and run in the philosophical direction with it, to ask yourself and admissions “What is zero as a concept, really, and what does it mean in the context of the world?” Whichever direction you choose to go, make sure that you offer a unique, thoughtful approach backed up by an anecdote or story that truly matters to you. You are being given an excellent opportunity to show admissions not only how you reason, but also what subjects – be it religion, philosophy, economics, or statistics – have shaped how you see the world. So as you take a stab at this question, make sure you artfully guide admissions through your own unique viewpoint.


Essay Option 3
The seven liberal arts in antiquity consisted of the Quadrivium — astronomy, mathematics, geometry, and music — and the Trivium — rhetoric, grammar, and logic. Describe your own take on the Quadrivium or the Trivium. What do you think is essential for everyone to know?
—Inspired by Peter Wang, Class of 2022

This prompt may sound a bit complex, but it’s really just a roundabout way of asking what subject or topic you love to learn about the most! If nothing comes to mind immediately, take a look back through notes and books from your favorite high school classes to see if anything jumps out. If you find yourself coming back to this prompt, try to focus on a subject that stokes your curiosity, a specific concept that has infiltrated your browser history, or an experience that has burned itself into your brain. Which kind of homework assignments were you always clamoring to complete first? Which topics want to make you open up a new book or hit play on a new podcast? Who challenges you to think of issues in new ways?

Whatever you think is absolutely essential for everyone to know, UChicago is aiming to bring self-motivated thinkers into their student body. Admissions officers want to know that you’ll be eager to contribute to lively class discussion, and maybe even conduct research in your latter years on campus. Show them that you’ll be a valuable addition to any classroom setting by getting specific — and maybe even getting them excited about a new topic!


Essay Option 4
Subway maps, evolutionary trees, Lewis diagrams. Each of these schematics tells the relationships and stories of their component parts. Reimagine a map, diagram, or chart. If your work is largely or exclusively visual, please include a cartographer’s key of at least 300 words to help us best understand your creation.
—Inspired by Maximilian Site, Class of 2020

This prompt is for all you artists out there, so pick up your pens, pencils, and compasses (both navigational and drawing) and get down to business. The first thing to note with this prompt is that UChicago doesn’t say the map or schematic has to be based in real life. So, if you’re going to get creative with an essay prompt, why not go all the way? How could you redraw the territories of Westeros so that the conflict over the Iron Throne never had to happen in the first place? What components or decks would you add to the USS Enterprise to help the crew go even more boldly where no one has gone before? This is a chance to show admissions your creativity both at a technical and written level. Whether you go realistic or high fantasy, make sure any diagram you present to admissions tells them everything they need to know about your unique passions and abilities.


Essay Option 5
“Do you feel lucky? Well, do ya, punk?” – Eleanor Roosevelt. Misattribute a famous quote and explore the implications of doing so.
—Inspired by Chris Davey, AB’13

When approaching this prompt, remember that you don’t have to use famous people as references for both the quote and the speaker. While the quote has to be well known in history or media, the quote’s attribution can be anybody from Ariana Grande to your own great-aunt. What sort of impact would hearing the words “Elementary, my dear Watson!” come out of your older sister’s mouth have on you? Do you consider yourself to be her Watson, a loyal steadfast friend who does their best to keep her humble and down-to-earth? You can use this prompt to show your creative side by rewriting history, or to tell admissions more about your background and what has shaped you into the person you are today. Both are great options — choose the approach that speaks most to you!


Essay Option 6
Engineer George de Mestral got frustrated with burrs stuck to his dog’s fur and applied the same mechanic to create Velcro. Scientist Percy Lebaron Spencer found a melted chocolate bar in his magnetron lab and discovered microwave cooking. Dye-works owner Jean Baptiste Jolly found his tablecloth clean after a kerosene lamp was knocked over on it, consequently shaping the future of dry cleaning. Describe a creative or interesting solution, and then find the problem that it solves.
—Inspired by Steve Berkowitz, AB’19, and Neeharika Venuturupalli, Class of 2024

The admissions department at UChicago wants to accept students who aren’t afraid to dream big or challenge the status quo. For this prompt, you have to think backwards to find the answer. Instead of trying to come up with a solution first, start by choosing a problem. If you can’t pinpoint something you’ve experienced yourself, then focus on the experiences of your friends and family, or even the world at large. Take inspiration from Sir Alexander Fleming, who accidentally created penicillin because he didn’t feel like cleaning up his lab before taking a two-week vacation (raise your hand if you can relate 🖐️). Then, once you’ve identified an issue, work outwards to find the elements you would need to solve it. You don’t have to think like a Rube Goldberg machine here — just remember that ultimately, the key to writing an excellent response to this prompt is in the details. Don’t just tell admissions about a problem and vaguely outline the potential steps to the solution; tell them why you want to solve it and how, and maybe even share how your answer could lead to more solutions in the future.


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 1-6 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!

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