I just went through the airfare shuffle myself. I tracked the cost of airfare from Chicago to Miami for over a month before buying. Some said that after the 60th day before your flight the cost goes down (not true). It fluctuates a lot. I found that it dipped a few times on Thursdays -weird. I'm planning on possible picking a few flights a year in advance and tracking the price throughout the year to see if there's any rhyme/reason to the pricing games. Anyway, I tracked the price along with the available seats -because I was buying 7 tickets at once and wanted the group seated near each other I had to buy earlier than I would have if it was just my fiance and I. But, by tracking the prices I knew I got an "average" deal. (Prices fluctuated about $150.) I think the closer to the flight date, the better the price, but you take a gamble on availability -espeically if you're picky about where you're seated or keeping a group together.
Also, use travel sites like Orbitz to find a flight, but book directly with the airline. It usually saves you $10/$20 per ticket.
My 2¢