University of Chicago Essay Guide 2020-2021

Essay Guides 12 min read
Photo courtesy of University of Chicago

In this University of Chicago Essay Guide, Bullseye Advisors Arielle and Caroline will cover how to approach the 2020-2021 University of Chicago supplementary essays. For more guidance on personal essays and the college application process in general, sign up for a monthly plan to work with an admissions coach 1-on-1.


Applying to University of Chicago

The University of Chicago prides itself on being a one-of-a-kind institution, and its application essays definitely exemplify that. Have you ever received a writing assignment in school, read the prompt, and just said to yourself, “what?” That’s how the UChicago prompts might feel. Much like the student body (who, along with alumni, actually write most of the prompts themselves!), the questions are quirky, intellectually curious, deeply thought-provoking, and often absurd.

In addition to the Common App, applicants to UChicago are expected to complete two essays (prompts below and here). The first essay is a fairly straightforward, “Why UChicago?” question. For the second, you’ll have the option of seven highly unusual and memorable prompts. Both essays are significant, but the second one might leave you a little baffled. Have no fear! These will likely be the most interesting essays you write in the entire college application process, so long as you give them the effort and thoughtfulness they require.

Arielle’s Guide to the Supplementary Essay Prompts

Although neither of the UChicago questions have a stated word count, a good length to aim for is in the neighborhood of 500-650 words.

Prompt 1: 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.

For a Why School essay, the key idea to get across is that you’ve researched extensively and thought about how you would fit in on campus. As a general caveat, be sure to keep the focus mainly on yourself and how you relate to the school — don’t just give general praise or tell the admissions committee about their school (and definitely don’t mention prestige).

Looking at the first part of the question, we want to address the learning: take some time to look through the Course Catalog, and mention specific classes you want to take that align with your overall narrative. If you have research interests, find professors you’re excited to study under or work for.

Next, think about the community: here, you can showcase exactly how you would contribute to campus (what RSOs will you join, or start?) and discuss UChicago’s unique, “quirky” culture. You could talk about school-wide traditions like Scav or Kuvia (maybe read up on some old master lists), and house activities and traditions like Chairman’s Cup, intramural sports, or the Karaoke Competition.

Lastly, we have the future angle: this could be where you think about your goals and lay out how UChicago will help you achieve them. What kind of skills, training, and preparation will UChicago equip you with? Why is this school the best place to set you up for success?

After you have a draft, read through to make sure you can’t replace “UChicago” with another school and have it still make sense — if you can, it’s not specific enough.

Prompt 2: Uncommon Essay

These (in)famous Uncommon Prompts (of which you’ll choose one) are one of the unique aspects of the UChicago application, designed to let students showcase their creativity, originality, and passion. They really are whatever you make of them, quite literally — you’re even allowed to write your own prompt, a high-risk/high-return situation (or use a prompt from any past year). My own essay was a stream-of-consciousness piece that zoomed in from the macro to the micro implications of the prompt; a friend wrote an academic, linguistic essay disagreeing with the premise of her question. It could be a short story, a letter, or have a visual component; it could be funny, heartfelt, or serious. If there is anywhere to take a bit of a risk on your application, this is the spot.

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).

To use their examples (for your essay, I’d find your own), a successful essay could be a short fictional piece about Sally on the seashore, fleshing her out as a character and creating a backstory; or, you could delve into the nitty-gritty on woodchucks, what it means to chuck wood, and try to come up with a calculation using some estimates and research on their per-minute wood-chucking rate. These are of course just two options — let your imagination run wild!

What can actually be divided by zero?

This prompt might appeal to a student interested in math — perhaps you could explore the various theories/results of dividing by zero (e.g. dividing by smaller and smaller numbers), adding your commentary on which one you buy most into. Dividing by zero is also generally known as a synonym for catastrophe — if you’re interested in history or politics, you could choose an analogous event or phenomenon like a power vacuum and draw comparisons.

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?

Here is where your passion for a particular academic topic can shine. If one of these areas is a cornerstone of your application’s narrative (and you haven’t already written extensively about it in your personal statement), this is a chance to delve into your passion and let your excitement be contagious.

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.

This prompt clearly lends itself to a visual component — if you’re visually creative or artistically inclined, I would take advantage. This could be anything; options could be a pushpin “conspiracy” board of photos and scraps that offers some insight into your identity, a map of your home or school or city labeled according to what each place means to you, or a family tree with hand-drawn portraits and anecdotes about members.

"Do you feel lucky? Well, do ya, punk?" - Eleanor Roosevelt. Misattribute a famous quote and explore the implications of doing so.

For this prompt, perhaps a student could attempt to elicit a laugh by creating a funny juxtaposition (and then perhaps elaborate on the particular circumstances that it could have come out in), or try to examine a complex interdisciplinary relationship between, say, a scientist and religious scholar. In the former situation, the “meat” of the essay would probably develop after choosing the quote and person; in the latter, one would probably choose the particular intersection they wanted to explore and then select the quote and speaker that would allow for the discussion. Both ways are equally valid!

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.

Despite the examples given, don’t feel pressured to present a revolutionary invention; you can still leverage the prompt to provide some insight into your life and personality. If you’ve spent significant time on a particular extracurricular, perhaps you accidentally found a way to complete a task more efficiently or significantly improve outcomes in some way. It could veer into the more technical or mechanical if that’s what your background is (although keep in mind the attention span and expertise of your reader). However, don’t feel constrained to your own experiences -- you could “find” the problem it solves in a sci-fi situation of your own invention.

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!

This prompt serves as a last bit of advice in what they're looking for! As mentioned above, creating your own prompt is a bit risky, but could result in a uniquely creative and standout essay. And if none of these year’s prompts are speaking to you, take some time to look through previous ones — there is a wide, wide range of topics. With the ingenuity and creativity you’ll use at UChicago, you can write a stellar essay for one that truly speaks to you.


Photo courtesy of University of Chicago

And those are the prompts! Now, here are Bullseye advisor Caroline’s top suggestions for crafting a winning University of Chicago application essay:

Caroline’s Top Suggestions and Advice

1. Be creative

These prompts are strange for a reason. UChicago kids are notoriously quirky, with a vast range of interests and passions. If you’re weird, it’s okay to be weird here. In fact, it’s encouraged.

Be creative in your responses, and don’t be afraid to take risks. I had one classmate whose essay was a theatrical script of an orange and an apple playing tennis. These essays can truly take any shape you want — don’t feel as though you have to adhere to a strict five-paragraph-essay structure or typical college application tone.

2. Showcase your curiosity

UChicago revolves around what we call the “life of the mind” and “rigorous inquiry.” It’s a place where intellectual curiosity and a love of learning reigns above all. We take this seriously: in fact, your first two years at UChicago will largely revolve around the Core, a series of fundamental courses in the humanities, social sciences, biological sciences, and mathematics that every student is required to complete. The central goal of the Core is to teach you how to think; therefore, Admission Officers are looking for students with that initial spark of intellectual curiosity.

As you read through the prompts for the second essay, I encourage you to take note of which one piques your interest the most. It may not be the prompt you confidently know how to answer right away, but if it makes you think, it’s worth exploring. By the end, your response should demonstrate a persistent curiosity to investigate and better understand the world around you.

3. Ask good questions

If there’s one thing that I learned at UChicago, it’s that the most pressing questions and important world problems rarely have a simple answer. A UChicago education teaches you to rigorously question everything and always be asking, “why?”.

In your essay response, don’t be afraid to ask more questions than you answer. Admissions officers are looking for someone with an insatiable intellectual curiosity, who will ruthlessly question the world around them.

On that note, don’t be afraid of the final essay option! The final prompt is always a “choose your own adventure,” in which you can pose your own question or select a previous year’s prompt. One of my best friends (who I met on move-in day our first year!) chose to investigate a favorite moral conundrum from Harry Potter. Sometimes the choose-your-own-adventure essays can be the most memorable for readers, since they pose a one-of-a-kind question and highlight the topics about which you’re most curious.

4. Argument matters more than vocabulary

College can feel like an intimidating place, full of scholars with PhDs who carry well-worn paperbacks of Foucault or Durkheim and use words like “antediluvian interlocutor” in casual conversation. Good for them, but you are not expected to do that!

Your writing must be thoughtful and clear, of course, and your grammar should be quadruple-checked, but the quality and depth of your thesis matters far more than impressing the reader with an advanced technical or academic vocabulary. My essay literally opened with the sentence, “If we’re going to be completely honest with each other, you should know that I spent an excessive amount of my Thanksgiving break watching television.” I then proceeded to analyze the Netflix show I had most recently binged. Don’t worry about impressing the reader with a lengthy, pretentious monologue; it’s far more powerful to have a clear, thoughtful argument.

5. Be genuine

Possibly the most important reminder. Admissions Officers read hundreds, if not thousands, of essays a day. They can sense insincerity from a mile away. As you’re writing, you might feel a pressure to come up with some massive life event that changed you forever; you might feel like you’re not simply not accomplished enough.

Release yourself from that expectation. Even mundane everyday experiences can be incredibly powerful. One friend of mine wrote about her part-time high school job at a local toy store, and how that influenced her concept of community. Your essay should sound like you, and capture how you view the world. The most compelling application essays showcase the applicant’s unique voice and how they came to have that perspective — don’t feel pressure to be someone you’re not.

6. Have fun (seriously)

Lastly, have fun with these prompts! I applied to a dozen schools, and the UChicago essays were by far the most interesting to write. If you’re struggling, don’t let it stop you: choose a prompt that jumps out at you, start writing, and see where your brain takes you. You’re going to end up exactly where you’re supposed to be, I promise.


This UChicago essay guide was written by Arielle Ambra-Juarez (UChicago ‘19) and Caroline Hutton (UChicago ‘18). If you want to get help writing your UChicago application essays from Arielle, Caroline, or other Bullseye Admissions advisors, register with Bullseye today.

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