Does anyone have any experience with Southwest flights out of Chicago? I'm thinking of flying in May, and right now there is a one way flight to Orlando for $104. Coming back on a Sunday the flight is min $144. Would you book now if you were me or would you wait? I've been trying to research it, but thought I would see if anyone has any insights for me. Thanks!

Thanks for the replies guys. I also looked at the Airtran flights and currently the same $104 from Southwest is $100 (with baggage fees extra) from Airtran. If that were to stay the same, I would book with Southwest, but I've been backtracking the same days of the weeks I'm flying and in earlier weeks the $100 from Airtran is $79. Did that make sense?? So, it's possible if I wait I could get the one flight for $79 (we plan on checking one bag--maybe two at the most so still a savings--but it is worth it to take the chance??)
Maybe you can use SW one way and Airtran the other??