Don't hesitate to check out smaller airports near where you live. I just booked Syracuse-Madrid via Chicago for $520 U.S. for late October to return mid-November (mid-week travel). Taking the same flights on the same days from Chicago direct costs $750 U.S. Go figure!! This could prove an interesting option along the eastern seaboard. Yes, it does take longer than one direct flight....but I think of that extra $230 I'll have in my pockets in Madrid!
I've always been amazed how often you see this type of thing. My first trip to Ireland on Delta I was booked to Shannon, the flight was direct from Atl to Dublin then back to Shannon, if I had purchased the flight to Dublin it was more expensive. My original plan was Dublin to begin with but was quite a bit cheaper to backtrack to Shannon then take a train to Dublin, I asked the airline (on phone) what would happen if I just got off the plane, they said it couldn't take off and would probably cancel out my return flight. While in flight I struck up a conversation with one of the flight attendants I told her my situation, she said to remain in my seat when we land and she would talk to some of the people she knew, to make a long story short she arranged for me to debark in Dublin, their only question was did I have checked baggage, since I travel the Rick Steves way you can safely quess my answer. Saved time and got myself an extra day in Dublin during the World Cup Soccer, fun night in Temple Bar!