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A Guide to the UChicago Supplemental Essays 2021-2022

  • Published On
  • August 3, 2021
  • Padya
Last Updated on : April 21, 2025
Read time: 9 mins
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A Guide to the UChicago Supplemental Essays 2021-2022

You probably already know that admission into the University of Chicago, with its acceptance rate of around 6%, 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 2021-2022.  

You don’t expect to see references to Costco or Harry Potter when you’re getting into the mindset of 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 unconventional 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 2021-2022.

The UChicago Supplemental Essays 2021-2022

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 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 2021-2022, 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 school? 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 2021-2022 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.

Option 1

What if the moon were made of cheese? Or Neptune made of soap? Pick a celestial object, reimagine its material composition, and explore the implications. Feel free to explore the realms of physics, philosophy, fantasy…the sky is the limit!

This question is quite straightforward, once you read it a couple of times. If you’re interested in astronomy, or even fiction writing, this is a great prompt to showcase your creativity. Think about celestial objects that fascinate you: it could be a planet, it could be the sun, or you could even choose an asteroid. What do you think the object of your choice could be made of—and why? You could choose a logical route to answer your question, referring to theories of math and physics to make your point. Or you can go the imaginary route and make a case for why the sun is actually made of chocolate chip cookies. As long as you “explore the implications,” you should be able to answer this prompt however you wish!

Option 2

What’s so easy about pie?

This is another open-ended prompt. Since, unlike the last question, the college hasn’t specified that you should use an academic or creative 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 smile. 

You could talk about an anecdote where an actual pie was involved. It could be the story of how you learned to bake—which would be a literal take on your response. However, you can also create a more elaborate metaphor about something else that equates the simplicity of pie to a broader incident. You can talk about anything—as long as you draw a conclusion about exactly what is so easy about pie. 

Option 3

In Homer’s Iliad, Helen had a “face that launched a thousand ships.” A millihelen, then, measures the beauty needed to launch one ship. The Sagan unit is used to denote any large quantity (in place of “billions and billions”). A New York Minute measures the period of time between a traffic light turning green and the cab behind you honking. Invent a new unit of measurement. How is it derived? How is it used? What are its equivalents?

The UChicago supplemental essays 2021-2022 can help admissions officers see how you might combine your creative and analytical sides. First of all, think about what you want to measure—and don’t be afraid to go out of the box. It could be the way to calculate the amount of maroon in UChicago’s logo, it could be a unit to measure the number of words in the average English novel. No matter what it is, make sure you go all out in explaining exactly why you’ve chosen to measure this particular thing, why it will be helpful, and how it is connected to other units of measurements.

Option 4

“There is no such thing as a new idea” – Mark Twain. Are any pieces of art, literature, philosophy, or technology truly original, or just a different combination of old ideas? Pick something, anything (besides yourself), and explain why it is, or is not, original.

This is a great prompt if you’re interested in the humanities. One factor to keep in mind if you tackle this prompt is to make sure that the subject has relevance to you. Since these essays help admissions understand what makes you unique and help them make their decision, think about how you can use your choice of topic to convey an interest or goal. If you want to be a film studies student, for example, you can argue why a particular movie is far more original than the other. If you’re a STEM student, you can also write about this topic! Make sure you’ve made your argument clear on exactly why or why not an issue is original.

Option 5

It’s said that history repeats itself. But what about other disciplines? Choose another field (chemistry, philosophy, etc.) and explain how it repeats itself. Explain how it repeats itself.

This question 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 discipline, but rather how you believe it repeats itself. One thing to remember is that thinking broadly about chemistry or philosophy would be a trap.

Option 6

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 “What can actually be divided by zero?” might appeal to you more than any of the new prompts for UChicago supplemental essays 2021-2022. 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 silly prompt with the plethora of options in your arsenal. 

While UChicago doesn’t prefer that you answer questions 1-5 rather than 6, carefully weigh your options before you decide to pick number 6. Is there nothing you might have to say for the first five 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 2021-2022, here are a few tips to help your brainstorming process: 

  • Standout essays for standout prompts: The prompts for the UChicago supplemental essays 2021-2022 are without a doubt, highly unique. It’s okay to feel intimidated, and you might choose a prompt that asks for a more academic-leaning response if you’re not a creative writer. While it’s fine 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 “pick something (besides yourself)” prompt or the topic of your choice questions, you can write about anything. So don’t restrict yourself to 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 2021-2022 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!

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