i like chicago's housing better because i wouldn't have to fly out, i could just do the grad apartments, but obviously that is a small concern hahaha
If you're shooting for academia, you should probably go to Chicago, unless your preference for Penn's "feel" was overwhelming. But keep in mind that the difference in atmosphere between Chicago and Penn might be indicative of the difference in atmosphere between an academic job and "real world" one. Depending on what it was about Penn that made you like it more, you might find that you like the academy less than you thought.
yeah, i did like penn's feel more, their community seemed happier and their lambda program is huge..which is important for me...they also have a lot of profs studying what i want to go into (sexual orientation stuff) which isn't the case at chicago, they pretty much only have nussbaum. and interdisciplinary opportunities seem better at penn, which with lgbt stuff is pretty important. but obviously chicagos placement for academics is like way better. so im torn.
I would say you'll want to go somewhere that you will enjoy for 3 years. Academia is really difficult to break into, even if you go to Chicago you have no guarantees. I definitely agree with JSMill that you may want to get a feel for that atmosphere. Obviously both schools are amazing, so you can't really go wrong, but if you have money considerations or just a feel preference, you may want to weigh those factors.