You'll need to get your ATP, first. It's the baseline requirement, especially in 2013 with the change in the law. Sounds like you are a ANG/Reserve pilot trainee, hang in there, bum for some Herk hours and check on GI Bill money for training money.

There should be opportunities in the Chicago area by then, regionals, lots of biz jets at MDW and more being sold there. ATP, take it from there
GF