I know UChicago has said somewhere that “no more than 500 words” are required for the “Why UChicago?” essay. That being said, do you think around 250 will be okay? I love UChicago but don’t want to sound like I’m reiterating reasons off of brochures/pamphlets.
Would anyone who has had experience with this mind reading my essay? 
I’m currently applying, and my “why Uchicago” is about 450 or so. I’m willing to read it and give feedback. I don’t think word could matters. It’s just content that matters. Of course, a long essay has the potential to have more good content.
I ended up rewriting my essay, and it was a lot longer once I wrote more in detail on things that I was interested in at UChicago. I applied EA, so decisions are (supposedly) out in ~1 week! best of luck to you! @ManaManaWegi
@tauisgood Thanks! I hope you end up somewhere great.