We are out of Chicago MDW and always go Southwest these days. It is just myself and DD26, so don't worry about seats together with no little ones. Of course, we prefer to be together and so far that's never been an issue. Sometimes we book EBCI for the early check in and better boarding section. Definitely really like the 2 checked bags fly free and no charge for my carry on! I book when they open the flight time for my trips, and then stalk SW(actually like that fun little game, lol), and always end up getting a much lower fare, usually close to $100 each way so I'm happy with that. I do have SW pts with my Southwest Chase card, and that really works well when I change to a lower fare, as getting points back I can use them at any time for anyone, instead of getting a credit that must be used within one year from booking and only for the person who's name was on the ticket. But, if I have to use cash instead of pts which we did once a couple years ago, I still appreciate being able to switch and get a credit instead of having to stick with whatever price I got at original booking! And we were able to use it for another flight so that worked well. So far, we've had no bad experiences and good customer service, so I'd definitely recommend SW!
.... I don't know what will happen next time though, as they have cut way down nonstop options, and have none after 4pm, which we like be able to choose sometimes for the way down to fly after school, to get there for example for the last day of FD. And of course to fly back as late as possible to have the time on our last day.
I haven't noticed the no non stops after 4 p.m., particularly on the way back from MCO to MDW. Always have several to choose from on the way back, for example on our day back in mid Aug, there are 7 after 4 pm. We'll take the latest at 10 pm, so we'll have almost like another whole day in the park, yay! Hopefully as we are out of Chicago that continues to stay the same.
I did notice though that they don't have much in nonstop during the week day afternoons which is disappointing. We're hoping for something around 2, 2:30 but there's only several connecting flights. I'd go morning, but DD26 is only taking off a half day from her job at school. So flying about 3:30 we get in close to 7. Hoping that when our actual Wednesday, Nov 8 date opens, they add some times. So far can only check Wed Nov 1st, although that did change from what I saw when just checking what times they were currently offering for Wednesdays. They were from a 5 something pm time getting in closer to 9, for times thru summer and early fall. I'd like to be able to maybe get in a few evening Mk park hours that night! With holidays coming I was hoping they'd be adding more nonstop afternoon flights when the next set of fare times open up.