JohnnyJet was recently on the show, and talked with Leo about how to stay informed about flight cancellations and delays during the holiday season.
First, Johnny recommends checking the weather of where he is and where he's going. He uses Weather.com and this traveler's weather page that he made. If there's disruptive weather, he'll then check the FAA's Flight Delay Information - Air Traffic Control System Command Center. He also signs up for flight status notifications offered free by each airline.
Johnny likes to follow his airline and airports on Twitter. His Twitter handle, @johnnyjet, has all sorts of lists of airlines and airports. You can get a lot of info on what to follow on Twitter using this page.
He also likes to keep track of his flights using FlightCaster.com. He puts in his flight 6 hours beforehand and it will let him know whether or not it's on time.
In case you're in a real bind and didn't book through a travel agent, CrankyConcierge.com will make other flight arrangements for you for a fee.