You just have to keep checking, and be sure to go to all the major airlines too. I got my best deal by checking daily at American, it did pay off. Seems the flights to San Juan are always on the high side.
sorry about the above post---i spoke too soon!. I just checked the jet blue airways site...they don't seem to have a boston to san juan option...but they do have a BURLINGTON to san juan (connecting in JFK) choice!---even better for u!
It's impossible to be of any help when I don't know where you're located or when you need to travel. There are almost always specials to everywhere on one airline or another, if you check sites daily. For instance, right now you can travel to San Juan from New York, Chicago, Miami, Fort Lauderdale and other places for as little as $138 a person roundtrip thru the middle of December and it's not usually the budget guys who post the big sales. It's the guys who aren't selling enough seats and don't want to fly an empty airplane. As a rule of thumb, the budget airlines run small sales because their prices are already beating the competition and they don't have a problem filling their airplanes. The big guys run super sales to take business away from the budget guys and to fill their airplanes. It's all a matter of economics.
The lowest on QIXO from Burlington on Continental is $368 pp roundtrip. I'm not sure you're going to find any deals through a small airport. We're driving 8 hours to Orlando to get a good flight to San Juan.
At the present time, the best you'll probably be able to do is around $360 round trip per person. If you hold off about 2 to 3 weeks, American and US Airways will probably run their usual winter sale from airports within an hour of Burlington, Vt. to several desinations including San Juan for about $150 to $200 round trip per person. When they do, it's likely some of the other airlines will also follow their lead.
The currents prices to Miami from New York are running around $200($178+tax and fees) on several airlines, namely American, Delta, NWA, US and United until mid-January. You can probably beat that in 2 to 3 weeks on a couple of airlines at around $150-$160 taxes included.