UChicago Supplemental Essay Prompts 2026-27 + How to Answer Them
Every applicant answers two questions: the required why-UChicago essay and the extended essay, choosing one of six options. Neither has a strict word limit (650 words is the practical norm). Every prompt below is quoted from UChicago College Admissions and verified against it on September 26, 2026.
Application: Common App or Coalition (UChicago supplement). Requirements can change during the cycle; UChicago's application portal is the final word on what to submit.
Question 1, required of all applicants
1 prompt
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.
How to answer
Address learning, community, and future with specificity. UChicago wants proof you know its particular character: the Core, the houses, the intellectual playfulness.
Draft this prompt in the essay tool →Question 2, the extended essay: choose one of six
6 prompts
Food for thought: How do thoughts eat?
How to answer
The extended essay is a writing sample, so wit and structure matter as much as the idea. Take the premise seriously and follow it somewhere unexpected.
Draft this prompt in the essay tool →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.
How to answer
Pick an artistic practice you know well and actually apply its principles to a problem. The elegance of the transfer is what gets rewarded.
Draft this prompt in the essay tool →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.
How to answer
Invent the metaphor, then defend it. The explanation is where you show how your mind works, so treat it like a short essay, not a one-liner.
Draft this prompt in the essay tool →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?
How to answer
A worldbuilding prompt: commit to the internal logic. Scoring and officiating details are where the humor and the thinking live.
Draft this prompt in the essay tool →AI: Allen Iverson. NASA, or the North American Saxophone Alliance. Share a potentially confounding, comedic, or captivating example of MIA (Mistaken Identity of Acronym) and tell us its backstory.
How to answer
Find a real acronym collision you can tell a story about, or invent one with a convincing backstory. The backstory is the essay.
Draft this prompt in the essay tool →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!
How to answer
The classic option. Browse past prompts in UChicago’s archive and choose one that connects to something real about you. Taking a small, controlled risk is what this option rewards.
Draft this prompt in the essay tool →Draft your UChicago supplement with feedback on every essay.
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