I flew it once and it was two times too many...I only flew Southwest once and it was a nightmare, never again.![]()

Among other things, the no-seat-assignment thing irritated me. I also hate going to Midway vs. O'Hare. Mileage-wise, Midway is closer to my house but O'Hare has direct access from the expressway(s) so the extra distance isn't an issue.
I never found them to be any cheaper than the other carriers when I had to travel for work; in fact, they were usually more expensive than either United or American, and the few times that Southwest was the cheapest option, I was able to justify booking on another airline either due to Southwest not being a direct flight, or the available flights were inconvenient.