2026-27 Cycle • 2 prompts

University of Chicago supplemental essays.

Every University of Chicago supplemental prompt for the 2026-27 cycle, with the word limit, what they're looking for, and the most common pitfalls.

1. Prompt 1: How does the University of Chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future?

   650 wordsrequired

   What they really want

   • Engage with the Core, the quarter system, and the 'life of the mind' culture by name.
   • Show you can do critical thinking on the page, not just claim to value it.

   Avoid

   • Generic 'fit' essay that could go to any school.
   • Listing programs without engaging with the intellectual culture.

2. Prompt 2: Choose one of the six 'extended essay' prompts (rotates yearly — examples include: 'In Homer's Iliad, the Greek hero Achilles dragged the body of Hector around the gates of Troy. Why do we drag things?' or 'Vestigial means having become functionless in the course of evolution. Tell us about something vestigial (real or imagined) and provide an explanation for its existence.').

   no limitrequired

   What they really want

   • No word limit, but 500-1000 is the sweet spot.
   • Be playful AND rigorous. Pure cleverness without depth fails.
   • Show how YOU think, not just that you can write.

   Avoid

   • Treating it as a creative writing assignment with no argument.
   • Going so abstract no one can tell what you're saying.
   • Ignoring the prompt's actual question while showing off.