Best University of Chicago Essay Prompts 2022-23

University of Chicago Essay Prompts Are Mindbenders

UPDATE: They’re here! The University of Chicago essay prompts are famous –and infamous. No other college asks applicants to stretch their minds this way. And they’re fun to read even if you have no intention of applying.

This year’s do not disappoint. For instance:

Essay Option 2:   What advice would a wisdom tooth have?
–Inspired by Melody Dias, Class of 2025

Essay Option 3:   You are on an expedition to found a colony on Mars, when from a nearby crater, a group of Martians suddenly emerges. They seem eager to communicate, but they’re the impatient kind and demand you represent the human race in one song, image, memory, proof, or other idea. What do you share with them to show that humanity is worth their time?
—Inspired by Alexander Hastings, Class of 2023, and Olivia Okun-Dubitsky, Class of 2026


As you read and maybe even consider applying to U Chicago, keep in mind:

Chicago’s prompts are invitations into your how your mind works, where it wants to go, places it wants to explore.

In general, supplemental essay prompts are a dialogue between the college and the applicant. Each college’s prompts are asking you to join in a conversation with its prompts. If the prompts don’t speak to you — if you don’t want to be part of the conversation with this college — move on to a college whose prompts “make more sense” or ask questions you want to answer.

Yes, these are often funny, but they are not jokes. OR maybe they invite you to deconstruct a joke. Or construct one. The university is giving you a preview of what you’ll be doing there. If that doesn’t appeal to you, there are lots more colleges to choose from.

Here’s what I’ve written in past years about these prompts AND the second required prompt from U Chicago, in addition to the Common Application Essay.

“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 an essay coach and a fiction writer, one of my favorite times of year is getting my eyes on their prompts. They’ve been called “quirky” “oddball” “creative” “impossible” essays. In fact, students can even invent their own or use application prompts from  years before.

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

 But if these prompts leave you smh, 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. Yale and Stanford each have different flavors of demanding essays.

But if you find these enchanting, keep reading. 

For better and worse, there are no word limits on these prompts — think 450-ish — and you must also answer a much more ordinary application 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.”

Keep in mind: University of Chicago is a Common App college. You will need to submit your Common App Essay and two Chicago supplements.

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

Whether the University of Chicago essay prompts are your cup of tea, I’ve got plenty of resources about essays and admissions throughout my website. Please take a stroll around.

To find out more about what I can do for you and your application, Please click here. To learn more about my values as an essay coach, please click here. And if writing the Common App Essay is still a mystery to you, try my recent posts here and  here 

If the University of Chicago essay prompts are on your horizon, shoot me an email or pick up the phone. I’m on the East Coast and open for business.

Liz@DontSweatTheEssay  1-855-99-ESSAY