American Airlines has most of the flights from SJU to STT. We paid $120 RT in July. Our flights were on time. The planes were twin props, and not the most comfortable, but this is a very short 30 minute flight. www.aa.com

Rod

Cape Air also flies from SJU to STT. And so does Seabourne. But these are really small planes.

We flew American Eagle from San Juan to Stt last month on a Tues and we were delayed for 5 hrs. All flights were delayed that day and it was a mess of people.
They said there were storms in Stt but we found out their flight crews were very late getting in that day. This has never happened before for us so it is just luck that your flight isn't delayed. American Eagle seats about 45 people.

My experience with American Eagle is their flights are often late, canceled for no reason, expensive, they don't wait for connecting passengers on delayed inbound American Airlines flights. American Eagle generally doesn't give a s*** IMHO.

Unless I get a good price on the ticket from ORD - STX flying American I prefer to connect using Cape Air in SJU. If you handle it correctly you can check your luggage straight through.

I also take the seaplane, but it isn't as convenient. You have to take a cab from the airport to old San Juan's waterfront. You can only take 30lbs of luggage on the seaplane. Any additional weight is charged at $0.50 per lb.

There are other carriers flying from San Juan to the VI.

Jim

Caribbean Sun runs similar planes to AA.
Good news with them was that they were less than AA and you could hold the reservation without them charging your CC, but bad news with them is that their seasonal schedules/flight times change without them notifying you so the flight you have scheduled at X time that you reserved months before may no longer exist when your trip rolls around.
I am not the only one this has happened to so dont build tight connections times with them months in advance. But if you happen to book the SJU flight maybe <90 or 60 days out, then maybe you can consider them.

I'm trying to avoid the Miami connection. I nearly missed my connecting flight home because the gate was blocked for 30-40 minutes, we had about a 1.5 mile run to get to the connecting gate, and they almost didn't let us on. I am never again going to get frustrated with people showing up late for a flight.

But, this San Juan idea doesn't sound much better. I would like to book my airfare for next summer soon. I'm guessing airfare prices will be going up substantially.

Deb, I’m not sure the San Juan connection would be any kind of improvement over Miami. We always seem to be delayed there. The bright side is there are many more commuter-type flights to STT from there, so you have some options if you miss your connection. But give me a direct to STT flight any day.