I am thinking about booking on SW if another good fare comes up. We live in Milw so would either have to pay to park or find a hotel with free parking and shuttle(we do this for Ohare). Anyone have any cheap but safe recommendations?
I've been looking at this as well. Do a Google search for "Park, Sleep, Fly Midway" and you'll come up with a number of options. Expect to pay $120-$150 per night.