I definitely prefer Midway over O'Hare. Midway is much closer to downtown Chicago - and there is usually less traffic congestion near Midway compared to O'Hare. Midway is smaller, and we started flying out of Midway because the airlines there (Southwest, ATA, Delta etc..) generally offered better deals than the larger carriers that fly out of O'Hare. I also find it fairly easy to navigate. Both airports have may choices for ground transportation if you need it (rental cars, airport express shuttle, taxis and the CTA busses/El trains). But as I said, I prefer Midway - it's much more convenient for us.