University of Chicago 2025-26 Supplemental Essay Prompt Guide

University of Chicago 2025-26 Application Essay Question Explanations

The Requirements: 2 essays of 1-2 pages each

Supplemental Essay Type(s): Why, Community

How to Write The UChicago Essays

This is it, the infamous UChicago supplemental application. These quirky prompts have been a rite of passage for generations of applicants, so before you dive in, just remember: if they could do it, so can you! Your goal in writing your UChicago extended essay should be the same as ever, to reveal something new to admissions. It might even help to have a few ideas in mind before reading through your options. These prompts are so specific (yet open-ended) and strange that, in the end, the key is just to follow your instincts. What speaks to you right away? What inspires you?

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.

Think of this run-of-the-mill Why Essay as the overture to your magnum opus (i.e. the Extended Essay). Chicago wants you to cover all the bases—“learning, community, and future”—so as with any Why Essay, it’s time to buckle down and do your homework. The more specific details you can incorporate into your essay, the more sincere and personal it will feel (and be!). Explore both academic and extracurricular opportunities. How will you pursue your interest in oceanography? With a major in Biology and a semester in Australia? What research opportunities will you pursue? Will joining the Club Crew team help you feel more connected to aquatic life despite your midwest location? One thing you won’t find on the school website, though, is that third piece, that “future” thing. Think about where you’d like to be five or ten years from now—your career, the impact you’d like to have, or even just a geographic location. How will a UChicago education help you get there? How will your scholarly and social pursuits help you grow? Show admissions how UChicago will be the bridge between the person you are and the person you hope to be.

Question 2: Extended Essay (Required; Choose one)

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

This prompt allows enough freedom for students with any interests to show off their personalities, logical reasoning, and creativity. If no particular animals or questions spring immediately to mind, grab a notebook and start jotting down animals in one column. Then, start a second column with attributes that you associate with each animal, such as the examples given in the prompt above. Which attribute(s) most captures your interest? Another way to approach this prompt is to list out topics, industries, or ideas that you’re interested in and then try to match a particular animal to each one. Do you love history? Maybe you’d communicate with elephants to mine their memories of major events. Are you fascinated by social hierarchies? Perhaps you’d like to commune with wolves about their pack structures. Remember—there is no wrong answer here as long as you justify the choices you make and reveal new information about how you see the world, what you’re interested in, and/or what’s important to 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 open-ended prompt leaves a great deal to the imagination while still demanding strong logical thinking. As you brainstorm your un-inventions, think about the chain of effects and which existing ideas or objects would fall apart without each invention, then choose the un-invention that you believe would have the most interesting and appealing impact. The less tech-obsessed among you may choose to un-invent something recent, like AI, smartphones, or the internet. Others might go more foundational and choose steam power, the printing press, or even the wheel. You can even posit ways that humanity might have built workarounds without this invention. (No wheels? Maybe everyone would travel by sled!) The older you go with your un-invention, the more ripples you’ll have to account for. Remember, the question is asking what you would want to uninvent, so make sure your response ties back to your personality, passions, and values. 

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

A highly philosophical question, this prompt asks you to think about not just words, but also roles or experiences you’ve had in your life that have contained their own opposite. While some of the earlier prompts relied more on logic, this one applies a creative lens to your own life experience. While some students will choose to define one word, others might more loosely explore roles or experiences they’ve had in their life that have contained their own opposite. For instance, perhaps as a stage manager, you’ve managed the actors and run rehearsals as an authority figure while acting as assistant to the director in a subservient role. Maybe your first solo road trip out of state to your grandparents’ house was simultaneously thrilling and terrifying. Remember that your goal here is not just to share about your life, but also to show that you’re able to engage in introspection, thinking deeply about the underlying meaning and duality inherent in some of your identities and experiences. Delve into these contradictions and show admissions that you contain multitides—and the maturity to recognize them. 

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

Option 4 serves as a counterpoint to Option 2; instead of removing something from the world, what would you save from its own imminent demise? You can approach this question by brainstorming small items that are quickly vanishing or by thinking of issues that are meaningful to you and what objects serve those causes. Perhaps you’d like to stop the world from exchanging restaurant menus for QR codes, as you believe the artistry and design of the menu reflects a restaurant’s unique personality and atmosphere; without them, each restaurant becomes more or less the same as another. Maybe you miss the handkerchief, both a sartorial accessory and a reusable tool for those with allergies, which can make an outfit pop while saving more tissues from landfills. What you choose to write about can be large-scale or small-scale, as long as you justify your response with a strong explanation of your object’s value in the world—whether that value is monetary, environmental, cultural, or personal—and a reflection that is personal to you. 

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

A great prompt for the business-minded among you, this question asks you to logically extend a company’s offerings in a seemingly unexpected new direction. To ace this prompt, you must blend creativity with logical thinking while highlighting something that is meaningful to you. Think about the example the prompt gives: Michelin Tires created the Michelin Guide to give people places to drive to in their cars, thereby using the tires the company sold. What other pivots can you come up with? Think of companies with a very clear product or brand and consider each step of their business plan. Maybe IAMS dog food will become a purveyor of natural pesticides to support dog breeders who need open, non-toxic space for their dogs. Perhaps Steinway will launch a wood-based packing peanuts product using wood pulp left over from building pianos. Don’t forget the last sentence of the prompt: How might a company’s product, customers, or supply chain help address what the world needs (and why is that need of particular interest to you)?

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

This is a great question for students who love data and those who can come up with a solid change of logic to connect seemingly crazy ideas. Hop on your favorite search engine to find the many websites that offer charts showing how things like butter consumption and US wind power generation line up. Can you come up with an explanation that would actually connect these two unrelated facts? Maybe the demand for butter in the US led farmers to care for more cows, and they needed an easy way to power more heated barns, so they started putting wind turbines on the edges of their fields. Have fun and let your imagination take off! Just remember that your goal with your correlation is to reveal a deeper truth about yourself, whether that be how your mind works or what you’re passionate about. 

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!

We love all the prompts from the past—there are so many quirky ones! If this year’s questions aren’t inspiring you, don’t be afraid to peruse the archives to find one that stands out to you. If you belong at UChicago, there is no doubt you will find a prompt that sparks a story within you. 

We’d also like to note that this is a great opportunity for recycling essays. If you wrote a strong longform essay for another school, see if any of the old prompts work in your favor, or make up your own question custom-built for your essay. Good luck! 😊