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!
I've included an example with each tip to show you how I'd approach the prompts.
You have five essay options or the chance to make your own topic.
Be detailed and thoughtful about each part of your argument or story.
For example, if I answered Essay Question #4, I might write from the perspective of the mantis shrimp about how he sees the world, or tell the story of a scientist who creates mantis shrimp "goggles" and sees the world for the first time like a shrimp. you can (and should) sneak in things that are important to you, too!
Look up the websites for the fields that interest you at UChicago.
You can usually find a list of professors, graduate students, upcoming and past classes, and research specialities.You can even take a look at the course catalog to see what's currently being offered for undergraduates and graduates in every field.In your essay, highlight professors' work that excites you or specific classes you'd love to take (not "Intro to..." classes, but workshops like, "I-Thou and the Subject of Psychoanalysis").Use the question as a launching pad to explore parts about yourself that you haven't addressed in your common app or the "Why UChicago" essay in a way that works.When you're brainstorming and outlining your essay, make sure the argument or story reflects something that's important to you or important about you.The strongest essays will tell a clear story or develop an argument with evidence.The admissions officers will be learning about you by seeing how you construct this argument or how you incorporate characters and language to tell your story.For the UChicago supplement, you'll have to write two essays: one answering a quirky prompt and the second explaining why you want to go to UChicago. When you take a look at the uncommon essay questions, you should laugh.The essays are meant to be fun, creative, quirky, and thought-provoking.If any of these interest you, explain why you think UChicago's flag grants, for example, would help you get a head start on your future research and career goals. Because you're quirky, you love to learn, you spend way too much time falling through the rabbit hole that is Wikipedia, you want to learn Econ from the masters, you...Let your sincere feelings about the college shine through!