University of Chicago's wording, checked October 26, 2026“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!”
UChicago sets no word limit: write as much as the answer needs and no more.
How to approach it
- 1If you write your own question, make it one you could only ask.
- 2Say clearly which prompt or question you are answering.
- 3Hold the same rigor as the other prompts.
A structure that works
One way to shape this answer. It describes moves, not sentences: the words have to be yours.
- 1The prompt you chose or the question you wrote, stated up front.
- 2Your answer, built with evidence and play.
- 3What the answer shows about how you think.
Mistakes to avoid
- Recycling a personal essay under a new title.
The checklist our grader uses for this question
When you check your UChicago answers, this answer is read against these 5 areas. Each comes back Met, Partly or Missing with a quote from your draft as evidence, and together with the no set limit limit they set its readiness verdict.
| Area | What a reader looks for |
|---|---|
| Answers the question | The opening sentences answer what was asked, plainly, before background or a hook; every part of a multi-part question is answered. |
| Takes the form seriously | It follows the prompt's premise and form (a note reads like a note, an imagined event has rules) instead of turning into a standard essay. |
| An angle of your own | The idea goes past the first one most applicants would have, with a specific, surprising choice. |
| Shows who you are | The play reveals the applicant's mind, values or humor; a reader learns something real about them. |
| UChicago's ask | States the past prompt chosen (or the applicant's own question) and answers it with originality and some risk. |
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Questions
More on UChicago and this kind of question
- Penn: A thank-you note · 50-200 words
- Dartmouth: Introduce yourself · 250 words
- Stanford: Letter to your future roommate · 100-250 words
- Northwestern: Painting The Rock · 200 words
- W&L: Option 4: the story of your name · 250 words