Supplemental essays are an essential part of any college application, but UChicago stands out among the top schools for its unique and sometimes mind-bending essay prompts. These prompts change each year and ask students to think in ways they likely haven’t for their college applications. Each is designed to give Admissions Officers insight into an applicant’s mind, and the way you answer can have a major impact on your admissions outcome. To give students the best chance of acceptance to their dream school, here’s InGenius Prep’s updated guide to the UChicago supplemental essays, featuring insights from Natalia Ostrowski, a Former Admissions Officer from UChicago.
The UChicago Supplemental Essays
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. 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 calls 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)
Option 1: “In an ideal world where inter-species telepathic communication exists, which species would you choose to have a conversation with, and what would you want to learn from them? Would you ask beavers for architectural advice? Octopuses about cognition? Pigeons about navigation? Ants about governance? Make your case—both for the species and the question.“
This prompt works best if you treat it as an intellectual exercise, not another personal statement. The key is to show your reasoning, not to retell your life story.
Think about how the species you choose reflects your curiosity. For example, engineers might ask spiders about their web designs, linguists might ask whales about communication, and economists could talk to ants about governance. Your answer should connect to an area of interest without simply repeating what you already wrote in your “Why UChicago” essay.
Natalia notes, “If you are interested in design, maybe you would talk to a beaver or a spider because they both create beautiful structures. If you are interested in governance, you might choose ants. The point is to make your case for why that species matters and what kind of question you would ask.”
To strengthen your response, go beyond picking the species. Imagine what the conversation would reveal about the world. What new perspective could humans gain from it? The more you use the animal as a lens for broader ideas, the more successful the essay will be.
Option 2: “If you could uninvent one thing, what would it be — and what would unravel as a result?“
This prompt asks you to think about the ripple effects of removing an invention. The challenge is that many students will gravitate toward the same answers, like nuclear weapons or AI. If you choose one of those, you need to add a unique angle—perhaps tying it to UChicago’s history with the Manhattan Project, or exploring surprising downstream consequences.
Natalia explains, “The first thing that comes to mind for many students will be the nuclear bomb. Obviously that will be a popular answer. But you do not have to choose something grand. It could be an object like an eraser or a fax machine. The key is what would unravel as a result.”
A strong response considers not just what would vanish but also what new challenges or opportunities would appear. For example, if you uninvent standardized testing, how would that change admissions, hiring, or the way we measure achievement? If you uninvent antibiotics, what would it mean for human survival and scientific discovery? Essays that follow the ripple effects into unexpected territory stand out.
Option 3: “Left” can mean remaining or departed. “Dust” can mean to add fine particles or to remove them. “Fast” can mean moving quickly or fixed firmly in place. These contronyms—words that are their own antonyms—somehow hold opposing meanings in perfect tension. Explore a contronym: a role, identity, or experience in your life that has contained its own opposite.“
Contronyms are words with opposing meanings, like “fast” (quick or fixed in place) or “bound” (headed somewhere or restrained). The trick here is not to get lost in telling a personal story but to analyze the paradox itself.
Natalia advises, “The point of this essay is less to talk about what happened to you and more to explore the tension between the two meanings.” If you want to connect it to your life, make sure the focus is on the complexity of the word rather than just the anecdote.
To elevate your essay, research examples of contronyms and choose one that sparks debate. For instance, “oversight” can mean both supervision and a mistake. How does that duality mirror how institutions function? Or “consult” can mean to seek advice or to give it. How does that tension play out in knowledge-sharing? An essay that dives into the intellectual and linguistic tension, while still tying in your perspective, will show Admissions Officers that you enjoy grappling with complexity.
Option 4: “The penny is on its way out—too small to matter, too costly to keep. But not everything small should disappear. What’s one object the world is phasing out that you think we can’t afford to lose, and why?“
This question seems simple but is actually one of the hardest. Students often default to sentimental items, but the best essays show why the object matters on a cultural or intellectual level.
Natalia explains, “Students will often default to personal keepsakes, but there are so many other choices here. Think about what the world is phasing out. Cash, physical media, phone books, dictionaries—why should one of those stay?”
A strong essay goes beyond saying, “I love books, so books should stay.” Instead, explore what they represent: permanence in a digital world, accessibility across generations, or resistance to the ephemerality of online content. You might also look at objects tied to tradition, like landline phones or libraries, and argue why their disappearance would mean more than just convenience lost. Admissions Officers want to see that you can take something small and use it to spark a thoughtful argument.
Option 5: “From Michelin Tires creating the Michelin Guide, to the audio equipment company Audio-Technica becoming one of the world’s largest manufacturers of sushi robots, brand identity can turn out to be a lot more flexible than we think. Choose an existing brand, company, or institution and propose an unexpected but strangely logical new product or service for them to launch. Why is this unlikely extension exactly what the world (or the brand) needs right now?“
This essay asks you to propose an unexpected but logical extension of a brand. It is not about business savvy, but about intellectual creativity.
Natalia says, “Think of it as a thought experiment, more like a paper than a personal essay. The point is to connect two things that don’t seem to belong together and explore why it actually makes sense.”
To succeed here, pick a brand you know well and take a creative leap. For example, could LEGO launch a mental health app rooted in play? Could Patagonia open a chain of community repair cafés? What makes the idea fun is not whether it could actually happen, but how you argue for it. Why is this what the brand or the world needs right now? If you can show cultural awareness and intellectual playfulness, you’ll have an essay that feels very “UChicago.”
Option 6: “Statistically speaking, ice cream doesn’t cause shark attacks, pet spending doesn’t drive the number of lawyers in California, and margarine consumption isn’t responsible for Maine’s divorce rate—at least, not according to conventional wisdom. But what if the statisticians got it wrong? Choose your favorite spurious correlation and make the case for why it might actually reveal a deeper, causative truth.“
This question is designed for students who like to think in unconventional ways. Your task is to take two seemingly random statistics and argue for why they might be connected.
Natalia explains, “This is not about being correct but about showing how you think. One of my favorite statistics is that traffic gets slower after an accident. It is not the accident itself that causes the slowdown, but the fact that people slow down to look.”
To write a strong essay, choose a correlation that sparks curiosity and has room for analysis. Then build your case step by step, showing how two unrelated trends could in fact reveal something deeper about human behavior, economics, or society. The more unexpected your logic, the more memorable your essay will be.
Past Prompts & “Choose Your Own”:
UChicago also lets applicants answer a past prompt or even create one of their own. This option sounds exciting, but it comes with risk. As Natalia cautions, “If you create your own, it has to be good enough. And whatever you do, don’t recycle your personal statement. That is not what these essays are for.”
In practice, the “choose your own” option often trips students up. Some applicants try to get too clever or overly personal, and the result doesn’t showcase the kind of intellectual curiosity UChicago values. Unless you have a truly original idea that sparks thoughtful exploration, it is usually best to stick with the official list of prompts.
Additional Tips for Writing the UChicago Supplemental Essays
Now that you’ve taken a look at the prompts for the UChicago supplemental essays, here are a few tips to help your brainstorming process:
• Standout essays for standout prompts: The prompts for the UChicago supplemental essays 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 toward 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 from the competition.
• 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!
While UChicago’s supplemental essay questions deviate from the typical prompts seen at most schools, these essays are still a great opportunity for students to stand out from the crowd! The way you approach these questions will give Admissions Officers a peek into the way your mind operates. Don’t just highlight your experience or focus on your personality. These questions ask you to explore ideas, and a compelling response can show Admissions Officers that you’re a free-thinker and a good fit for the UChicago community.
If you need further guidance from an admissions expert, InGenius Prep is here to help! Our team of Former Admissions Officers from top schools like UChicago know how to approach these questions. We can help you craft the perfect application and get you one step closer to that acceptance letter. Book a free strategy call and get started on your admissions journey today!