When are you going that those prices are SO high? If you have more than 3 months, definitely wait this one out.
And even if you are within 3 months and your dates are too firm to change, fly. I would never drive to Chicago just to hit SWA. (Although I do wish SWA would get themselves up here and fly to MCO so we could get some competition)
I believe a fair price from MSP to MCO, if you book early enough, is between $200 and $250. At $500, I'd be seriously considering travelling other dates, or waiting to buy plane tickets, if I had a choice.