Adrianne is a Senior Admissions Counselor and TV/film director, producer, writer, and actress currently based in LA. She uses her experience in multiple disciplines to help students achieve their personal and academic goals.
Welcome to the supplemental essays for the University of Chicago! UChicago is known for having some of the most creative essay questions of any college, but it’s easy to misinterpret them as casual opportunities to write about the first thing you think of. You’ll need to have a discerning eye for what sort of responses will make a positive impression and which will blend into the crowd or stand out as too strange. Writing great responses will take significant planning and refined communication in addition to out-of-the-box thinking.
But first, a typical essay prompt.
Table of Contents
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.
This is a fairly standard “Why here?” question. As you know, it’s important that you be very specific about your desire to attend the colleges on your list. There’s no recycling an essay you wrote for somewhere else. This one needs to be all about how your “wishes” fit with the opportunities available at UChicago.
Your task here is to show UChicago that:
You know what you want to study (make a major up if you’re actually undecided—just choose what makes most sense based on your past experiences).
You can talk about some upper-level classes you’d like to take at UChicago (in line with your academic direction. Don’t mention anything readily available at other universities—pick something interesting and unusual.
You can mention a few professors you’d be interested in working with (again, who teach in a subject related to your academic path. These should be tenure-track professors, or at least professors you know will be there for the next four years. Not sure how the vicious academic hierarchy works? Ask us.
You have a sense of which extracurricular clubs you’d like to be a part of (do your research—the clubs you choose to discuss should be a logical extension of your past academic and extracurricular achievements).
You have identified any other academic or extracurricular opportunities that UChicago and the area will provide you with.
Again, this essay isn’t just about UChicago. It’s also about you. Make sure you’re relating what you want to do at UChicago to your past experiences—that the professors and courses that interest you will help you build on your most impressive achievements.
Question 2: Extended Essay (Required; Choose one)
Let me preface my discussion of these different questions with a few remarks. Every year, UChicago does a fabulous job of providing its applicants with remarkably creative prompts. One of the effects of their selection of quirky questions is that it is extremely difficult to provide general guidance on how to respond. In other words, they’ve done a great job ensuring that your responses must be authentic and spontaneous. My number one recommendation here is to approach these like puzzles. Give them some thought. But if nothing occurs to you after a few minutes of meditation, move on to the next question.
Essay 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.
Inspired by Yvan Sugira, Class of 2029
We’re starting off strong with a creative, playful prompt here that could still give you the space to talk about issues that matter most to you! Even if you’re not interested in an academic field that works with animals, you can still think about the questions and problems that are most interesting to you and then think about the animals that could be associated with that. I’d also recommend you think a bit bigger than just talking to your family dog or the squirrel in your garden (although you could still take that in a cool direction).
This isn’t so much a prompt about the animal that you choose, though; it’s all about the reason why you chose to talk to them and what that elucidates about your personality. What great mysteries about the world could talking to a wild animal help illuminate for you?
Essay Option 2
If you could uninvent one thing, what would it be — and what would unravel as a result?
Inspired by Eitan Fischer, Class of 2027
This prompt asks you to identify a problem (or simply a phenomenon) and then work backward in history. Think about the things that you encounter in your daily life and where they came from — you could go more in the direction of solving larger social issues (e.g. you uninvent the iPhone, and you decrease the negative effects that screen time has on young people’s brains), or you go in a more fun direction. What happens if you uninvent chairs, or peanut butter, or socks? There’s not a wrong answer here, as with all of these questions, so go in the direction that feels authentic to you.
Essay 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.
Inspired by Kristin Yi, Class of 2029
This may seem like it’s just an option for the linguists and language enthusiasts, but it can suit anyone who feels like they’ve existed with some cognitive dissonance, which is probably everyone at some point. But the more significant the dissonance and the lessons it taught you, the better. It’s also a bit more of a serious option than some of the others on the list, so if the really quirky prompts intimidate you, this might be your best option.
To write this one, identify an aspect of your identity, role, or experience that has held two opposite truths at once: leader and follower, belonging and alienation, success and doubt, independence and reliance. Explain both sides of the contradiction and why they coexist, then dive into how navigating that tension has shaped your self-understanding. Your goal is to illuminate a paradox that feels deeply personal.
Essay 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?
Ella Somaiya, Class of 2028
The key to this essay is to start small and think about the little things in your day-to-day life. But you don’t want to just choose something random — it should connect to a bigger idea or concept you want to tackle. You can choose something fun or quirky, but help us see the bigger picture and go beyond nostalgia: explain the cultural, emotional, or functional value the object holds and what would be lost if it vanished. The strongest essays connect the small to the big, using the object as a metaphor for something human you believe is worth preserving. This prompt is about attention, care, and the significance of the seemingly insignificant. Why is it considered insignificant, and why should it not be?
Essay 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?
Inspired by Julia Nieberg, Class of 2029
This question isn’t asking you so much to critique a brand, their position on issues, or their products. It’s asking you to think about a company stepping into a seemingly odd and unexpected space — and in a way that it positively impacts the world. While you’re potentially talking about larger social issues, you can have fun with it. What if American Airlines got into the jewelry business? What if the people who made Stanley Cups started a film production company? It can’t be completely random since the extension of this brand needs to have a point (that’s where your cleverness comes in!), but the more unexpected, the better.
Essay 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.
Inspired by Adam DiMascio, Class of 2025
In a similar fashion to some of the above essay options, this prompt is asking you to draw unlikely comparisons, now just with statistics. And as with the other options, choose the larger idea and/or issue you’d like to talk about, and then find some statistics that can be a vehicle for your larger topic. Bonus points, as always, if it lends itself to a good, creative hook. Then, find that possible correlation, and figure out what it means to you. Use imaginative logic, pseudo-science, cultural analysis, humor, or metaphor, but make the case with conviction — show how your mind connects dots others dismiss.
Essay Option 7
And, as always… the classic choose your own adventure option! In the spirit of adventurous inquiry, 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!
Now, obviously this all boils down to, “Write whatever you like.” The Common App does this with their final prompt, too, so you’ll sometimes catch a break and be given the option to “write whatever you like.” Notice, however, that UChicago, as always, does something a little different. You can choose one of the many past prompts or “create a question of your own.” If you choose the latter route, actually write out your question. And believe me when I say it had better be as inventive as the ones that UChicago proposes.
As always, Ivy League college admissions consultants are here to help. Don’t hesitate to reach out.
