The Best University of Chicago Application Essay Prompts 2021-22

Calling all applicants to the University of Chicago:

What if the moon were made of cheese? Or Neptune made of soap? Pick a celestial object, reimagine its material composition, and explore the implications. Feel free to explore the realms of physics, philosophy, fantasy…the sky is the limit!

As a college essay coach and a fiction writer, one of my favorite times of year is getting my eyes on U Chicago’s newest batch of supplemental essays. Famous — or infamous — for its “quirky” “oddball” “creative” “impossible” supplements, U Chicago is looking for students who are turned on by questions like these

What are they looking for with these kooky questions? They want to know how you think, what you think about, what you care about, and how comfortable you are with questions that do not have straightforward answers. They’re interested in ambiguity, uncertainty, creativity — thinking not just outside the box but in people who create new boxes.

If these prompts leave you smh — or you’re just not that into them — that might be a message from the universe that the University of Chicago isn’t the right place for you. That’s valuable information. Move on. There are dozens of other outstanding colleges with more straightforward essay prompts.

But if you’re enchanted by questions like these from the newest list of prompts, keep reading. U Chicago is such a “quirky” “oddball” “creative” place, that you can even pick a prompt from previous years!

There are no specific word limits on these prompts — think 450-ish — and you must also answer a much more specific 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.

But the fun — if this is your idea of fun — is in these krazy kwestions — all provided by students!

What’s so easy about pie?
—Inspired by Arjun Kalia, Class of 2025


In Homer’s Iliad, Helen had a “face that launched a thousand ships.” A millihelen, then, measures the beauty needed to launch one ship. The Sagan unit is used to denote any large quantity (in place of “billions and billions”). A New York Minute measures the period of time between a traffic light turning green and the cab behind you honking. Invent a new unit of measurement. How is it derived? How is it used? What are its equivalents?
—Inspired by Carina Kane, Class of 2024, and Ishaan Goel, Class of 2025


“There is no such thing as a new idea” – Mark Twain. Are any pieces of art, literature, philosophy, or technology truly original, or just a different combination of old ideas? Pick something, anything (besides yourself), and explain why it is, or is not, original.
—Inspired by Haina Lu, Class of 2022


It’s said that history repeats itself. But what about other disciplines? Choose another field (chemistry, philosophy, etc.) and explain how it repeats itself. Explain how it repeats itself.
—Inspired by Ori Brian, AB’19


In the spirit of adventurous inquiry (and with the encouragement of one of our current students!) 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!

If UChicago is on your horizons and you want some help starting these essays or you want help with essays for any other college or university, shoot me an email or pick up the phone. I’m on the East Coast, and I’m open for business 🙂  1-855-99-ESSAY