I think the time of day is the key here. I flew out of Midway last Wednesday. Had a 9:00 am flight, so I was there by just before 7:00. Used curb-side check-in, which was a breeze. When I walked inside, the check-in lines there were pretty long, so using curb-side probably saved a good 20-30 minutes. The lines to go through the security scanners were probably 20-30 people deep (with about 4 or 5 lines open). They needed to hand-check all laptop computers, which slowed things down a bit. but I'd say I was through there in about 15 minutes. So I was in the gate area by about 7:15-7:20 or so. Not too bad at all (except for the long wait, a gate change (from the new to the old terminal), and a 40 min flight delay).