Just some ideas for booking airfare.
1) Tickets are sold at different rates depending when you buy them. Typically it is about 45 days in advance, 21 days in advance, 14 or 10 days in advance. Keep an eye out.
2) Don't buy airfare on the weekends, they are typically more expensive. The prices tend to drop on Tuesday or Wednesday and then go back up on Friday for the weekend.
3) If you like Southwest, definitely get the DING program. You have to keep a constant eye on it, but the prices are very good. They usually have a morning and afternoon DING fares for various locations.
4) If you are in the ballpark of what your willing to spend on airfare (about $10-$20 per ticket), don't wait for the "better deal" because it might not come. With the fluctuations in oil prices and the bulk in which airlines buy, you might not see the price go down and you'll lose your shot at a good airfare.
5) Know when you are traveling and how busy it can get. Airlines work on supply and demand. If the demand is high, they have no reason to be overly competitive on prices. For example, people travel like crazy at Thanksgiving. However, the next few weeks after Thanksgiving the airfares dump because no one is going to travel again until closer to Christmas.
I was able to get good airfare from New York 21 days out through Southwest. I never saw the same prices on airfare again until it was 10 days out from my proposed travel date. By the next day, the flight was booked.
Good luck.
