Looking at a return flight through PHL (AA). I know there's a change of terminals, but I have 2 hours, Global Entry and no checked bags. The price and traveling time are both pretty good, so I'm probably going to risk it. Just wondering how bad it might be

Did that a month ago, no issues at all.

With two hours and no checked bags you should be fine. Just keep an eye out for AA schedule changes that could reduce your layover time (common at PHL), or flat out cancellation of your return flight because of a number of reasons (also has occurred at PHL). Just curious why you just don't fly Jet Blue from Logan to SXM directly. They still have that flight, don't they? If the savings was that significant I suppose I could understand why you would want to deal with a connecting flight. But, if the savings are less than $100 each way I would choose a direct flight every time.

No direct flight on Sunday. And the cost ($1,326 is ridiculous) is ridiculous. Jetblue has become just another airline taking advantage of a tragedy (Irma) to gouge its customers

Tim--got to say, Jet Blue was always 'just another airline'..

I definitely like JetBlue BUT I am not married to them. IF you have other choices then they only "take advantage" if you buy their tickets. This (and last) year I didn't...

All airlines typically charge higher prices on Saturdays and Sundays. Next time around check out their prices on Tuesday or Wednesday, if a mid-week flight works for you. This is just my opinion, but Jet Blue has never let me down. Their standard seating has more leg room, and their choice of refreshments is superior over the Big 3 domestic airlines. Good luck and hope everything goes as planned for you.

Tim,
I travel regularly internationally from the DC area. I have used Southwest into BOS to leverage lower fares or better flights to the EU. I have not had any problems connection from my SW flight to an international flight. You might consider using SW to FLL or other hub leverage a convenient non-stop to SXM. Just a thought.

I'm actually connecting through FLL on JetBlue on my flight down, and got a pretty good deal. It was the return flight, that was a problem. Almost everything was requiring an overnight someplace on the way home or was priced outrageously. I was considering an extra day in SXM to take advantage of cheaper Monday flights, but it seemed that the expense of an additional night in SXM would eat up any savings, and booking a single night in SXM can be a problem in January. There have been rumors of South West adding SXM - don't know what's holding them back. I think they capture the market.