Instead of a text field, UChicago asks you to upload the file with your essay. Would it be an awful idea to illustrate one of my essays? I feel as though they might appreciate the creativity, and they’re all about risk-taking, but it IS an essay…
What do you mean by illustrating your essay?
I think it would depend on the subject matter. Make sure there’s no limit on the file size, since embedded images can add to that.
Like you said, it’s a risk. I read an article one time that mentioned someone who had the prompt, “Ask yourself a question; then answer it.” The person asked “Do you play the tuba?” and answered, “No”. Some admissions officers loved it. Some thought it was lazy.
Unless you’re some sort of an art major, the school probably cares more about how you write than your drawing skills, so I wouldn’t personally recommend it, especially if you’re set on the school. It might come across as overkill.
UChicago is quite quirky, so they might appreciate it. Maybe you could structure the essay around a drawing?