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I fly every month or so and here's my typical process:
1. Search the travel sites like Kayak and Expedia to find a good time/price combo that works (I never buy my tickets through the travel sites, I always go straight to the airline to purchase... had some problems in the past). Southwest and some other airlines don't participate in these sites so be aware of that.
2. Once you find the flight you want, check it daily and watch the price and seat availability. If the number of free seats drops you might want to buy earlier before its all booked up.
3. I watch the price and if its dropping, I don't buy as long as it is still consistently dropping. The day that price starts going back up again is when I buy them. This means I don't get the tickets at the cheapest price they hit but I'm real close and a lot better off than when i started searching.
4. If you think you're going to start flying alot get one of the airlines credit cards with the airlinr you fly most. This gets you at least 1 free checked bag usually and priority boarding which is pretty nice.