When you write your essays for UChicago, don’t necessarily go for quirky because if you try too hard, that’ll shine straight through. Write them honestly and make sure they actually encompass who YOU are. Like other posters before me have said, they look for fit because UChicago is a unique school with a certain philosophy. Chicago students are well known for learning for the sake of learning and not to just get a degree. They tend to be a little weird – in the best of ways – and always up for a midnight debate or two. They seem to actually have fun – despite what their image is to outsiders – and their definition of fun might be different from a different school’s definition of fun. Everyone has a different definition of fun, so whether UChicago is or isn’t fun is dependent on the person.
Overall, don’t necessarily worry about what UChicago is looking for in an applicant. If you meet the quantitative requirements (in the GPA, ACT/SAT score range), then put yourself out there as yourself in your essays. Don’t try to come off as someone you’re not because in the end, it might come back to hurt you. If you fit and its meant to be, it’ll happen. Have fun with it, and good luck!! 