Midway is a great airport. I've never been delayed at Midway, and indeed have almost always taken off and arrived early. The boarding pass check and security are set up perfectly to allow everyone to get through the process in a short amount of time. Parking - close parking - is plentiful and remarkably easy to navigate.
Southwest is a great airline. I love, love, love Southwest. I love that every leg is priced separately - I can purchase two one-way tickets and a round-trip ticket on Southwest out of Midway for cheaper than one one-way ticket out of Cedar Rapids. I love that there are no baggage fees unless you are checking more than two bags or bringing something over 75 pounds. I love the new method of boarding that rewards you for checking in early. I love how they stress customer service while allowing their employees to bring their own individuality to their jobs. Case in point: The flight back from Philly had the roughest landing I've ever had. You know how you always bounce slightly when you first touch down? We bounced three times, throwing you out of your seat (thank God for seatbelts) then rushed down the runway far faster than you should. When we finally came to a stop, the attendant came on and went "Wheee! That was fun!" The guy next to me muttered "That wasn't fun", and I agreed, but I liked how the attendant handled it.
That guy next to me? Huge. HUGE. Took up his seat, half of mine, and half of the guy on the other side. Now, I know I'm not a small man. But still. I was pressed against the window for the entire two hours of the flight. Thank God for books.
Carry-on people. You know, folks, if you have to stand there, pounding on your bag, moving it back and forth and to all different angles to try to get it into the overhead compartment, well maybe - maybe - YOU SHOULD JUST CHECK THE DAMN THING!!! As I was boarding for the flight back, there was a woman who had the whole line stopped because she was trying to get a bag that was literally - I'm not exaggerating, because she was right in front of me - six inches wider than overhead compartment. Don't get me wrong - it's not that the bag would normally be six inches wider, it's just that she had it so jammed filled with stuff that it got that way. Eventually she saw the line forming, pulled the bag down and ducked into the row so people could get past. She might have been the worst offender, but she wasn't the only offender.