Yes, I know, the saying that U of C is "Where the squirrels are more aggressive (and better looking) than the women!" and all of the other T-Shirts, but I've not been to a more fun campus since.
Where else can you walk out across the quads at 4:00 a.m. on a major university campus after a night of hard research work and stumble into the middle of a medieval melee with swords and armor being carried out in a language that you don't understand, complete with torches? (Old English? High German? Didn't know, didn't speak it.)
Where else can you spend a weekend with fellow students driving around America like maniacs (driver's seat) while doing research through piles of travel guides and almanacs to find the random stuff on the scav list (passenger seats)?
Where else can you expect the barista at the campus coffee shop to know more about Sartre, Gadamer, and Hegel than the philosophy Ph.D. candidates and more about applied linear dynamics and combinatorics than the math majors?
Where else can you get drunk with the major authors of major monographs at a bar *under the campus* with an on-the-wagon bartender serving over a hundred beers and ridiculous prices ($2.00 a bottle for things that cost $12.00 a bottle int the store when I was there), and ultimately take them home crying on your shoulder after you've argued about the finer points of their research for several hours?
On the other hand, at its worst it's also a stuffy, pompous, judgmental, hyper-competitive place.
But I can say that if you thought it was boring or unfun, you just weren't trying. I had a blast at U of C, and that was as a stuffy old graduate student!