University of Chicago 2026-27 Supplemental Essay Prompt Guide

University of Chicago 2026-27 Application Essay Question Explanations

The Requirements: 2 essays of 1-2 pages each

Supplemental Essay Type(s): Why, Community

How to Write Compelling 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)

Food for thought: How do thoughts eat?

Inspired by Ernest Leong, Class of 2026.

To ace this prompt, you’ll need to apply both creative thinking and logical reasoning. Imagining thoughts as independent living beings, consider what nutrition or fuel they would need to survive and how they would take that food in. Maybe, like humans, they need a mix of vitamins and minerals supplied by your bloodstream, or maybe your answer is less biological, with thoughts feasting on new ideas or puzzles and riddles, headscratchers that force them to contort, expand, and wrestle. What do you feed your thoughts and how do you keep them satiated? For that matter, what is a “healthy diet” vs. “junk food,” and do our thoughts need both to survive? This prompt may appeal most to those of you who love collecting facts or are fascinated with psychology. Regardless, your response should give admissions insight into the way you think.

The James Webb Space Telescope, launched in 2021, utilized origami-inspired techniques to compactly store and deploy its sunshield in space. Choose an artistic practice and use its principles to propose an elegant solution to a problem.

Inspired by Akhil Korra, Class of 2028

This prompt is great for both the artists and the problem-solvers among you. You could approach this in one of two ways: either start with artistic practices you know well and think about their principles or start by identifying problems you’d like to solve and try to connect those to artistic fields. The problem you’d like to solve can be mechanical, cultural, or anything in between. Maybe you’d apply the collaborative and inclusive nature of community signs to bring together groups of people at war and cultivate understanding. Perhaps you know that prepping a canvas is as important as your paint color choice and think that the same concept could be applied to city planning. Remember that, at the end of the day, this essay is about you, so whatever you choose to write about should tell admissions something about your artistic interests and/or the societal or business problems that keep you up at night. 

Sometimes metaphors get mixed up. For one reason or another, one could say, “we’ll burn that bridge when we get there” or “the world is your china shop”. Make up your own mixed metaphor. Explain how it could make sense, be understood, or even applied.

Inspired by Julia Nieberg, Class of 2029

This prompt should appeal to the word nerds among you and those who look at the world through an unusual lens. If you choose this prompt, you can start by jotting down metaphors, aphorisms, and sayings that come to mind, then see how you might combine them as in the prompt above: “The world is your oyster” and “like a bull in a china shop” became “the world is your china shop.” This could mean that the world is full of valuable and fragile things for you to enjoy, but you must be careful to protect and care for them (like the environment, perhaps). Any combination can work, no matter how far-fetched or wacky, as long as you have a clear idea of what it might mean. Apply your creative and logical thinking, have fun, and remember: don’t cry over a molehill! 

The Olympics have long celebrated the pinnacle of human athletic achievement. But what if they expanded to honor the mundane? Imagine a new Olympic event built around an everyday activity like speed dishwashing or competitive grocery bagging. How is it scored, officiated, and judged? Why is it a worthy addition?

Inspired by Ewan Smith, Class of 2028.

This prompt seeks to learn about both what matters to you in your daily life and how your brain works to organize the rules of your competition and defend its inclusion in the Olympics. Think about what you might want admissions to know about you or what values are important to you. Maybe you often babysit your younger siblings and have elevated their bedroom routine to a fine art. Your competition could be a bedtime quadrathlon, including bath time, tooth-brushing, pajama-donning, and storytelling—each judged on speed, degree of completion (did they reach all their molars?), and mood of your young charges at the end of the phase. You can choose a lighthearted event (like packing your backpack in the morning) or a serious event (like helping your grandma make doctors’ appointments), as long as it means something to you and you take the time to break it down into some sort of sporting rubric. Just make sure you answer the last piece of the prompt: Why is this new event worthy of inclusion in the Olympics? What skills or abilities does it test, and why are those important to celebrate on the international stage? And don’t forget to have fun with the playful nature of this prompt! 

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! 😊