It seems like most people I've talked to are only giving themselves a week or so to acclimate to the city before classes start, which seems kind of weird to me.
I would not be able to do this. OK, I am exaggerating slightly, but I need more than a week or two in order to get a sense of my environment. I'd likely perish on Survivor due to this fact.
I plan on moving out to Chicago within 2-8 weeks (yes, quite a large time frame, but it's difficult researching housing from a different state). That way I can settle in and be at ease as much as one can be come 1L.