Well we have an airport with a lot of competition (BUF), so the airlines play around with the fares quite often in an effort to get the bookings. I usually just book SW or JB. I check the seats on JB site to see how full/empty the plane is to help me decide if the prices will go down or up. I am travelling at the end of March and have only booked my departure flight so far. If it's under $200 one-way, I normally book it, especially if it's SW because I can get credits if it goes down. However, if it's over $200, then I wait it out. However, all airports are different and I'm not sure how much competition there is at yours. I suspect being Boston there might be quite a lot? Have you priced out other airlines to compare...