Actually Chris there are several airlines based out of ORD and MDW who are hiring. (whether they will be when you get done with college may change).
These include Mesa, Skywest, Republic and GoJets (all of whom fly for United as United Express). American Eagle (flies regional jets for American Airlines and is a wholly-owned subsidiary of the company). Southwest Airlines has a crew base in Midway. Skyway airlines out of Milwaukee is a good option also for a beginning regional pilot job. You don't go from college to a major airline like United or American. You first have to get years of experience flying cargo, or flight instructing and then work for a regional airline. You would usually need several thousand hours of flight time before getting an interview with a major airline. And by the time you have that kind of experience American/United will be different companies than they are today. United is currently recalling it's furloughed pilots and I've seen projections that they will be hiring off the street in the next year or so. They may be hiring again, or may have merged with other airlines... who knows.
As an airline pilot you do NOT need to live in the base where your company puts you. A lot of pilots commute (including myself until recently - I'm now based at ORD). Commuting means travelling to/from work on your own time by either driving several hours to your base or jumpseating to work. For example I used to be based in Charlotte NC. If I had a 4 day trip starting on a monday at 6am then I would need to catch a flight to Charlotte sometime on Sunday and then buy a hotel room for the night. Commuters try to bid for trips that are "commutable" meaning the schedule allows you to travel to/from work without buying a hotel. Clearly living in base is preferable.
Commuting is a significant factor when you are talking about time off also. You spend a lot of your off time waiting around in airports trying to get on flights home etc...
As far as time off goes though, it depends on which company you work for and how senior you are. Mesa gives it's junior pilots a minimum of 8 days off each 28 day schedule period. Other companies give much more time off as a minimum. My last company maxed out at 14 days off/mth for the most senior guys. My current company has schedules which have anywhere from 12 days off for the junior guys to 21 days off a month for the really senior guys. You get paid a minimum monthly pay guarantee of usually around 75hrs/mth whether you fly or not. If you fly more than that you can make extra pay. There are also other ways to make extra pay like picking up "open time" on a day off - flights that the company has not got covered.
As for school - you do not need a degree in aviation - and most regional airlines don't require you to have a degree at all but having one will help make you competitive when it comes to getting a job. There are other ways to go though. There was a First Officer hired at my company last month who has only been a pilot for 9 months! 9 months! Wow. She went to a full-time flight school in Florida where she got all her ratings in 4 months or so. Then she went to a bridge program where she paid to do training in a Canadair Regional Jet, and this enabled her to get an interview with the regional airline of her choice even though she had less than 600 hours flight time. Now she is working on her degree while working as a pilot and building seniority. This path shaved years off getting to a regional. Not for everyone, but there are definitely other options than going to college for 4 years first.
http://www.atpflightschool.com/ was the place she went I believe. I have worked in a 121 training department and they love to hire people who did these bridge programs because they usually do well in training.
Well I hope i've had some useful info for you.