I've been checking every possible way of getting to Orlando as cheaply as possible. I hit the Air Canada website - was quoted $3,500 for 4 seats in mid-December. I then went to Expedia.ca, and found 4 seats from Wpg via Toronto, for $2,300 and change. The strange thing is, they were Air Canada flights!
If you're considering a drive to Minneapolis to fly out of, check out Skyauction.com. They have packages for auction that often have flights from Minneapolis and I've seen some great deals.
I'd be interested to hear what you finally decide. Living here in Winnipeg doesn't get us many deals, does it?! From what I've heard, there are no direct flights out of Winnipeg to Orlando planned for this winter.
Jane