I live in Philly, and contrary to popular belief I think it's a great place to live with some affordable housing options. During integration (the beginning of every month) where you'll finish a four-day trip, followed by one day off, then immediately into a two-day trip that has a 4:30AM show...you'll be happy that you live in base. I would think commuting from ORD would be tough. There's a high likelihood that on a given day there will be some kind of weather issue either in the midwest or the east coast...or both. So you'll be dealing with EDCT's, GDP's and cancellations a lot. A lot of people do that Chicago commute, and they seem to make it work though.