How to Write the UChicago Supplemental Essays 2020-2021

Padya Paramita

A Guide to the UChicago Supplemental Essays 2020-2021

You probably already know that admission into the University of Chicago, with its acceptance rate of only 7.9%, is far from guaranteed. But as you gear up to apply, you might get further thrown off by the essays you have to write. Alongside the required classic “why UChicago” question, this highly selective school also presents you with some rather unusual prompts in the UChicago supplemental essays 2020-2021.  

You don’t expect to see references to Costco or Harry Potter when you’re getting into the mindset for convincing admissions officers why you’re a good fit for a school, and yet these have been part of past UChicago prompts. It goes without saying that UChicago’s quirky prompts aren’t your typical supplemental essay questions. But despite their unique nature, the goal of the university is the same as any other school -  to understand your perspective, to get a sense of your goals, and determine whether your values align with those that UChicago looks for in its students. To guide you through each of the prompts, I have outlined the questions, how to go about tackling them, and more tips to help you write the UChicago supplemental essays 2020-2021.

The UChicago Supplemental Essays 2020-2021

UChicago prides itself on its thought provoking supplemental essay prompts. Use these as an opportunity to introduce yourself, what you’re passionate about, and your ambitions and goals. Although there is no set word limit for any of the prompts, InGenius Prep counselor Natalia Ostrowski, who worked as the Assistant Director of Admissions at UChicago, recommends that you limit the first essay (“Why UChicago”) to a page (double spaced in 12 point font). The second essay - the more weird and unusual one of the two - should be about two pages, double spaced and in 12 point font. 

The voice in your essay can be serious, you can let your creativity completely loose, or you can find an in-between take on any issue you’re writing about. According to Natalia, “UChicago admissions officers want to see how you connect ideas and get a front-row view into your critical thinking, intellectual curiosity and excitement for knowledge.” 

So without further ado, let’s go through all of the prompts - including each of the odd ones - for the UChicago supplemental essays 2020-2021, and ways you should dissect and answer them:

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.

Although there is no strict word limit on this “why UChicago” essay, don’t go overboard with what you like about the university. Admissions officers already know it’s a great school. How do you narrow down what you love about the college? Well, look at the question for hints. The question asks that you elaborate on how UChicago can help meet your needs when it comes to the following:

  • Learning
  • Community
  • Future

When reading your response to this question, admissions officers are looking for whether you’ve done your homework on UChicago to determine how much you’d fit into the college. Below are a few questions that Natalia suggests you ask yourself to brainstorm for this essay:

  • Why is the Core important to you? (And don’t just copy/paste what you wrote for Columbia and vice versa — they’ll know) 
  • What specific majors are you interested in and why? 
  • Has it always been your dream to work with [insert professor here] or study abroad in [insert location here]? Why? 
  • Which activities are you excited to contribute to? Why do you want to be a Maroon (yes, UChicago has sports!)?

Emphasize the community aspect - how do you hope to find your people on campus? Is it 

the opportunity to participate in student organizations such as Humor Magazine or the intramural wiffleball team that call out to you? Or are you keen to explore Chicago’s Revival Community Improv Theater within walking distance of the college? You might want to continue your community involvement work from high school by participating in the Neighborhood Schools Program, The Civic Knowledge Project, or one of the college’s several organizations that help give back to the greater Chicago community. 

Since you have space, you can provide context on who you are, your passions, and the kind of values you hope to bring to UChicago. Whatever you choose to write about, make sure you prioritize what you’re looking for from your college experience and how UChicago is the ideal place to explore these interests or goals. Show admissions officers that you have done your research and can convincingly argue for your place at the school, clearly outlining the parts of campus you wish to commit to.

Question 2: Extended Essay (Required; Choose One)

Now we get to the more peculiar essays. At first - and even second or third glance - these questions are out of the box in comparison to other schools’ supplemental essays. But where do you even start? Natalia affirms that, “Admissions officers want to see how your brain works. It doesn’t matter what you write about or which question you answer — your ideas and how you write about those ideas is what matters.” 

She also adds that from your essay, “Admissions officers will be able to have a glimpse of who you might be in the classroom, or when you’re deep in discussion in the dining halls or dorms, or walking through the snowy Harper Quad on your way to get some hot chocolate at Hallowed Grounds.” 

The takeaway for admissions officers reading your UChicago supplemental essays 2020-2021 should be to understand what makes you tick and how you are going to contribute to the community. This is the goal you should keep in mind throughout your writing process.

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

This is one of the most open-ended questions among the UChicago supplemental essays 2020-2021, because with a convincing enough argument, you might just be able to sway admissions officers to believe - or not - that a certain tongue twister has an answer that we might not have thought about before. Here are some tongue twisters — with questions ingrained in them — to help get you started on your brainstorm:

  • Peter Piper picked a peck of pickled peppers. How many pickled peppers did Peter Piper pick?
  • Can you can a can as a canner can can a can?
  • She saw Sharif's shoes on the sofa. But was she so sure those were Sharif's shoes she saw?
  • Which witch switched the Swiss wristwatches?
  • To begin to toboggan first buy a toboggan, but don't buy too big a toboggan. Too big a toboggan is too big a toboggan to buy to begin to toboggan.

Don’t get so caught up in the tongue twister that you miss the second half of the question: “method of your choice.” Use this question to discuss your potential major or interest, because after all these are your supplemental essays. How can a certain law in physics explain if you can “can a canner?” Does the law of demand and supply in economics help answer the question of “How many pickled peppers did Peter Piper pick?” This is a great question to combine both your imagination and creativity alongside your curiosity within your academic interest.

Essay Option 2

What can actually be divided by zero?

—Inspired by Mai Vu, Class of 2024

This is another open-ended prompt. Since, unlike the last question, the college hasn’t specified that you should use an academic subject to explain your answer, your options are truly unlimited in how you choose to answer the question. This prompt isn’t one where you should bring up your academic interests unless they flow in organically. But it is a great opportunity to show your humorous side and make the admissions officers laugh.

You can reflect on a real-life incident that occurred that helped you have a certain realization, or you can be more hypothetical and come up with your own math problem. Whatever you choose, it’s crucial that you explain why you’ve drawn a certain conclusion. What does “being divided by zero” mean to you? Why do you believe X object cannot actually be divided by zero? Since there are no specifications, you can use a concrete object such as chairs, or a more abstract example, such as happiness or grief.

Download Every Supplemental Prompt Here!





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 from the UChicago supplemental essays 2020-2021 is a great place to show the school that you’re not afraid to tie everyday mundane things to academic areas. Think about how you use topics such as astronomy or grammar in daily life. To tackle this prompt, you could talk about a particular mathematical formula that you believe everyone should know. Or you could take the Trivium route and explore how grammar has evolved over time.

Remember though, that you are encouraged to get as creative as you want with these, so if you want to use examples from a language that originated in a fantasy novel or film that you enjoy, you could take that risk. This question, like prompt 1, leans in a more academic direction than the others - since it explicitly brings up fields that you’d study in school and/or college. So if you’re not a fan of creative writing, this question might be more approachable for you since the answer can be framed with a scholarly angle. Whichever approach you choose, make sure to not emphasize the question, “what is essential for everyone to know?” but rather why you believe it’s important for every single person.

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

If you’re an artist, or a visual thinker, this could be a great prompt to attempt. Since the question doesn’t specify whether the map you create can be from a real or fictional place, you can go all out and pursue anything you like. It can be on a smaller scale — such as your neighborhood growing up, or far bigger such as the entire continent of Asia.

One factor to keep in mind is to make sure that the subject has relevance to you. Since these essays help admissions understand what makes you unique and helps them make their decision, think about how you can use your choice of map to convey an interest or goal. If you want to be a computer scientist for example, you can reimagine the map for Silicon Valley to your convenience and explain why you’ve done so.

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

This is definitely a more lighthearted prompt among the UChicago supplemental essays 2020-2021, that allows space both for creativity as well as a chance to demonstrate your interest in a particular topic. You could, for example, take a quote from The Office or a well known internet meme and assign it to someone such as Albert Einstein or Abraham Lincoln. The more important aspect of this prompt is the second half of the question: the implications of misattributing a quote. How is an industry — or even the world — impacted if someone who is reputable has their viewpoint misunderstood? 

This can be a particularly interesting topic to explore if you’re keen on English or journalism, as students applying to UChicago often are. What are the consequences of misquoting someone? Take the quote and persona you’ve chosen and imagine how the world — or a community — would be shifted if people start believing that they used an uncharacteristic statement. Analyze how such an incident can shift dynamics, through a lens that you’re passionate about, such as sociology, politics, or literature. 

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

UChicago appreciates students who “dig deeper, push further, and ask bigger questions” — and this question is an effective way to demonstrate that you have the traits that the school looks for in its students. Think carefully about what you wish to cover here — there really are no limits on your topic as the prompt suggests that your solution can be creative. Don’t be afraid to think out of the box. For example, you might find the perfect answer to the question of “milk first or cereal first?” by discovering a solution that explains exactly why one is more efficient than the other. 

By explaining what the solution is — and its subsequent problem — you not only get to apply your knowledge and understanding of a topic, you get to kill two birds with one stone and convey your area of interest to the admissions officer as well. For this prompt, I’d recommend having a third party read the essay to see if the logic you’ve used in solving the problem does indeed make sense. You don’t have to be scientific at all in your explanation - you just have to convince the reader.

Essay 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!

If you don’t like any of the other options, why not look at 30 of the previous years’ questions that UChicago has provided to inspire you. The question “How are apples and oranges supposed to be compared? Possible answers involve, but are not limited to, statistics, chemistry, physics, linguistics, and philosophy” might appeal to you more than any of the new prompts for UChicago supplemental essays 2020-2021. And that is okay. 

Note that UChicago is giving you an incredible amount of choice here by providing access to their past prompts. If you decide to go the alternative route and come up with your own question, it HAS to be good enough. It wouldn’t be the wisest decision to go with your own lame prompt with the plethora of options in your arsenal. 

While UChicago doesn’t prefer that you answer questions 1-6 rather than 7, carefully weigh your options before you decide to pick number 7. Is there nothing you might have to say for the first 6 essay questions? If that is indeed the case, and you’re willing to take the risk (and UChicago appreciates risk-takers) put your unique spin on a previous - or completely original - question!

Additional Tips for Writing the UChicago Supplemental Essays 2020-2021

Now that you’ve taken a look at the prompts for the UChicago supplemental essays 2020-2021, here are a few tips to help your brainstorming process: 

  • Standout essays for standout prompts - The prompts for the UChicago supplemental essays 2020-2021 are without a doubt, highly unique. It’s okay to feel intimidated, and you might choose a prompt which asks for a more academic-leaning response if you’re not a creative writer. While it’sfine to find an option that’s tailored towards your assets, note that other applicants will be writing all sorts of weird and highly imaginative essays. So you need to come up with something memorable and original to stand out among the competition.
  • Consider multiple approaches - Each of the questions for the UChicago supplemental essays 2020-2021 have different routes you can choose. For some, such as the “misattribute a famous quote” prompt or the topic of your choice questions, you can write about anything. So don’t restrict yourself into thinking there is a right answer. While it might feel like the college may want you to answer a certain way, UChicago wants to understand your personality and background. Stay true to yourself and authentically convey who you are and the way you view the world.
  • Don’t let the prompts discourage you from applying to the school - While the prompts set by the University of Chicago are definitely unusual and undoubtedly tricky, they are not impossible to answer. The school has set a standard for similarly quirky questions and hundreds of students still get in every year. So the minute you see these on the Common App, don’t be tempted to run away and remove UChicago from your school list. It’s a great school, and if you have a strong application to compete with other top students, don’t miss out on the chance just because the supplemental essays seem a little intimidating!

    The UChicago supplemental essays 2020-2021 can add depth to your application and help admissions officers understand who you are and what you’re looking for from your college experience. The “why UChicago” prompt is your chance to convey how you would be a good fit at UChicago and vice versa. On the other hand, the essay question is a great component to capitalize on so that admissions officers understand your interests, creativity, and how you view the world. The task at hand might seem like a tough uphill battle, but it’s definitely not impossible. Good luck!

    Schedule a free consultation

    to find out how we can help you get accepted.