So, your states you're in New York. If you're NYC area, a few quick thoughts from my experience:
1) Most of the LCCs suck at serving NYC. Like almost don't bother level bad. United, Delta, and American are all highly competitive.
2) Fly American or Delta out of LGA or JFK, but if you want EWR fly United. For JetBlue, JFK only. Many more options that way.
3) Round trip to MCO is almost always cheaper if you hit the minimum stay requirements. You can check two one-ways, but don't be surprised if it's more expensive.
4) Don't forget about HPN, sometimes you can get cheap tickets, and it's a much easier airport to deal with IMHO.
5) LGA is under construction, build extra time into your travel if you decide to use it.
And a little bonus thing: if you're upstate but near Amtrak, especially near the line going to Albany, the best bet is to take Amtrak into NYP, then take the NYCAirporter shuttle van to your airport of choice (you could also take the 4/5/6 to Fulton St then jump onto an A train to JFK, but only if you're really penny pinching). If you have to connect from upstate, doing Amtrak to an airline is a better experience for parking and just in general than trying to get a good flight out of ALB or similar.