We live south of Boston (between Boston and Providence) and we always fly out of Boston. I know that other nearby airports can be much cheaper sometimes but Boston has the most direct flights as far as I can tell.
We usually fly with Delta and usually pay $200 or $215. We've never lucked out and gotten the good sales. I just can't wait till much closer to by my vacation as I want good times and non-stop so I buy mine pretty early on.
Well, this year for our trip in Oct/Nov, after we firmed up our dates and resort, I started checking like I always do: Orbitz and Delta and Expedia and right here everyday.
One day at the end of January, I read a post here about AA having a big sale for people in the Northeast going in the Fall. So I ran over to AA.com and Orbiz.com and low and behold, I got in on the sale! I got 4 non-stop tickets at great times for a total of $410!!! That has NEVER happened to us before. We lucked out!
I guess what I'm trying to say is shop around and often at Orbitz and Expedia to see what they're going for each day. Read here too. If you're like me, then just book it if it's what and when you want it for or you could wait till it gets closer and they have sales but I just can't do that! Plus your going over a holiday so maybe prices won't come down and it will fill up quickly...
I believe Southwest flies out of the smaller airports in Hartford, Ct; NH, and Providence. They usually good deals but I don't know about non-stops.
Good luck and sorry I rambled!