I heard recently that the cheapest fares are generally available Tuesday through Thursday and that it's best to book four to six weeks out. Travelocity and Expedia (and I'm sure others) offer fare alert and fare tracking services that might be helpful. Also be sure to check each airlines baggage fees, as they can add up if you plan to check baggage. You'll save money if you can stick to just a carryon. If you see a fare you can live with, jump on it and then don't look back. In my experience, you can really drive yourself nuts if you keep looking at fares after you've bought your tickets. One other suggestion (although this likely won't help you at this late date) is to use one of Capital One's credit cards. Their airline points program is easy to use and has no blackout dates. I have friends who charge everything they can to earn points (and they are disciplined about paying their balance every month).