Unless you have a really creative idea, pick one of the five set prompts.
Read through all the essay prompts before picking one.
You're applying to colleges, so you might think you should talk about yourself and your extra-curricular activities, like in a typical personal statement. It seems obvious, but be sure you're answering the essay question!
For example, if I were writing Essay Question #3, I would make sure I've answered all three parts of the question, so ultimately, the admissions officer would have an idea of what I think history is, who "they" are, and what "they" aren't telling us.
You may not have thought of anything like these questions before, but that's okay!
University Of Chicago Essay Length
The UChicago supplements are a great chance for you to step back from the typical admissions process, think about something different, and express yourself creatively.
There's no wrong answer or incorrect approach for these prompts.
Be creative, use descriptive language, and have fun!
The UChicago supplemental essays might throw you off at first.
The questions are strange, quirky, thought-provoking, and definitely daunting.