You mentioned you are from Central Il. How far away are you from Midway Airport? Last August our family flew out of Midway and back for less than $100 round trip. If you keep checking flights and can fly on Tuesday, Wednesday, or Thursday, you can find great deals.
Never mind, didn't read the whole thread. Now just keep checking your flights. They change multiple times per day, and it's so easy to change a flight when it's cheaper.
There are "Park, Sleep, Fly" hotels near midway. They offer free long term parking + shuttle to and from Midway. For $120, I bet you would be pretty close to the cost of one of those hotels.