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University of Chicago
Why UChicago plus one famously weird extended essay. Annotated guidance.
What UChicago rewards
UChicago asks for two essays: a required Why UChicago, and one extended essay chosen from seven famously strange prompts (the inter-species telepathy one, the contronym one, and so on). Both are recommended to run one to two pages, and UChicago is test-optional with a no-harm policy for 2026-2027.
The extended essays are the most distinctive prompts in American admissions, and that is the point: UChicago is screening for a particular kind of mind, one that treats a weird question as an invitation rather than a trap. The trick is not to be quirky for its own sake. It is to take a strange question completely seriously and follow it somewhere real. This guide covers both essays, with an annotated Why UChicago and a worked approach to the extended essay.
Essay prompts for 2026-2027
2 prompts for UChicago, each broken down with annotated examples.
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