One tip I can give you right off the bat - fly out of MDW! You can do midweek fares out there virtually anywhere for a good price!
I'll need to travel there from BDL (Hartford, CT) later this summer. Fares are ~$200 with no Saturday stay.
Where are some of the cities you are heading to?
------------------
"I will not be pushed, filed, stamped, indexed, briefed, debriefed or numbered. My life is my own."