Good luck on the airfare. I live in Central Massachusetts and have been shopping flights for my trip a couple weeks before yours. I usually fly on Southwest out of Manchester, but will go out of Logan if I can find a decent price. I have friends that live in Manchester and drop me off at the airport, so parking was never an issue. If I fly out of Logan, I park and take the T into the airport because parking at Alewife, Riverside or Woodland is only about $4 a day.
This trip I ended up booking out of Logan. AirTran for the flight down, JetBlue on the flight home. My round-trip price was $234. Southwest's current fares are comparable to that.
I've actually never used Priceline, as most times I'm planning a trip and would prefer to have control over my flight times. At one point I could have booked JetBlue both ways for about $170, but it would have been a late flight into Orlando, and an early flight leaving to come home, so it would have mostly wasted both days. I prefer to fly down in the morning and home in the evening, and at least get a half-day on both days.
The only time I'd use Priceline is if I'm flying somewhere where flight times didn't matter as much, like flying to my parents' for the holidays.
-Rob
