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Eloquent & Wacky: How to Write Standout 2020-2021 University of Chicago Essays

Besides the required “Why UChicago” essay, the University of Chicago has an extremely unusual set of prompts for its second required essay. Or, as they describe them, a series of choices that are “eloquent, intriguing, or downright wacky.” UChicago gives you seven (actually, more, but we'll get to that) options suggested by students.

They're definitely out-of-the-ordinary, but we hope you'll agree they're also a lot of fun. This guide will show you how to do well on both essays, how to choose the "wacky" prompt that's best for you, and hopefully, how to keep UChicago's spirit of fun and adventure going as you work on these. 

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: In the past, U of C has suggested aiming for about 500 words.


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 seven prompts for the “extended essay.”

Six of these are new prompts inspired by submissions from UChicago students and alumni; the seventh is a gateway giving you carte blanche to choose a past University of Chicago essay prompt or even create your own. The options are truly limitless.

Let’s take a look at the choices, and then 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)

Note: There is no word limit. However, in the past, UChicago has suggested keeping to 650 words or fewer. 

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

Option 2: What can actually be divided by zero?

—Inspired by Mai Vu, Class of 2024

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

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

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

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

Option 7: 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!

Note on finding past prompts: While many are listed on UChicago’s application page, Prompt found even more of them here, thanks to a Reddit thread. Even better, you can check out our specific advice for each of the options UChicago gave in 2018-2019 and again in 2019-2020.


How to decide which prompt to write?

First, get your creative juices flowing with a quick brainstorming session. Run through each option (except maybe #7), and jot down anything that comes to mind. Take a short break, and then try it again. (Did good ideas come to you during your break? That tends to happen.) These questions are so off-beat, a looser approach might get your in the right mind-frame. 

Secondonce you've generated a few good thoughts, take the opposite tack. Think about the totality of your application, in conjunction with the question: Will you succeed spectacularly at UChicago and beyond? With that filter in mind, think about whether one of these prompts will allow you to bolster an important message about who you are, or what you can or want to do, or perhaps help counter a potential weakness. (Maybe it's showing off some math/logic skills in one of your responses if your math grades are on the lower side.)

Finally, 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 get writing, consider that once you're accepted you'll be able to inspire one of next year’s "eloquent, intriguing, or downright wacky" University of Chicago essay prompts.

Click here for our guide to writing the Common App Essay



Prompt’s Essay Specialists reviewed 13,000 admissions essays in 2018, helping thousands of students submit their applications with confidence.

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