Buying plane tickets at their lowest price is all about timing. You want to try to buy within 2 to 1 week before the actual flight.
Being from the Westcoast, I typically fly America West because they offer the lowest fares and have the most variety of flight times.
http://www.seatguru.com/
This site is a must to find more information on the airline and type of plane you will be flying in. Seriously check this site before purchasing a seat. If you have to spend $300, make sure its an airline that offers inflight entertainment and comfortable seats
For example I recently flew on Northwest Boeing 757 (300) and on the way back 757 (200). Northwest has got to be the most bare-bones service out there. No inflight entertainment, the seats on these plane are super packed, they don't even offer peanuts with their drinks. I paid $333 for those tickets too. They deserve to be bankrupt.
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In contrast, I flew across country on a Delta/Song 757 for $198, the seats are leather, plenty of leg room, and each one comes with its own Direct Satellite TV.
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BTW Boeing is coming out with its new 787 DreamLiner. It has alot of new feautures,for instance, the cabin humidity will be increased from 5% to 15%. Simulated day and night time. I can't wait to fly on this thing.