$89 Find Cheap Flights from Caribbean Islands to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Boston departing on 2/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$115
Overall average: $169
Frontier
Thu 2/26Sun 3/1
SJU - BOS • Non-stop
Cheapest non-stop
$104
Typical prices: $135-$315
Spirit Airlines
Fri 1/23Mon 1/26
SJU - BOS • Non-stop
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Flight Deals
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Flight Deals

Cheap Flights from Caribbean Islands to Boston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean Islands to Boston

Thu, Feb 26 - Sun, Mar 1
Frontier Logo
6:00 am - 9:19 am
SJU
-
BOS
4h 19mnonstop
Frontier Logo
10:04 am - 3:00 pm
BOS
-
SJU
3h 56mnonstop
$115Frontier
Sat, Feb 14 - Fri, Feb 20
Multiple Airlines Logo
6:00 am - 9:19 am
SJU
-
BOS
4h 19mnonstop
Multiple Airlines Logo
3:00 pm - 8:06 pm
BOS
-
SJU
4h 06mnonstop
$116Multiple Airlines
Fri, Jan 23 - Mon, Jan 26
Spirit Airlines Logo
10:52 am - 2:12 pm
SJU
-
BOS
4h 20mnonstop
Spirit Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
$119Spirit Airlines
Sat, Jan 17 - Sun, Jan 25
Spirit Airlines Logo
10:52 am - 2:12 pm
SJU
-
BOS
4h 20mnonstop
Spirit Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
$120Spirit Airlines
Fri, Jan 30 - Sun, Feb 1
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
Delta Logo
8:55 am - 2:00 pm
BOS
-
STT
4h 05mnonstop
$225Delta
Thu, Jan 29 - Wed, Feb 4
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
Delta Logo
8:55 am - 2:00 pm
BOS
-
STT
4h 05mnonstop
$226Delta
Thu, Jan 29 - Sat, Jan 31
American Airlines Logo
2:54 pm - 10:56 pm
STT
-
BOS
9h 02m2 stops
American Airlines Logo
6:05 am - 1:55 pm
BOS
-
STT
6h 50m1 stop
$234American Airlines
Thu, Jan 29 - Wed, Feb 4
American Airlines Logo
2:26 pm - 8:30 pm
STT
-
BOS
7h 04m1 stop
American Airlines Logo
6:00 am - 2:36 pm
BOS
-
STT
7h 36m1 stop
$235American Airlines
Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
12:22 pm - 11:59 pm
POS
-
BOS
12h 37m1 stop
JetBlue Logo
6:15 pm - 7:17 am
BOS
-
POS
12h 02m1 stop
$243JetBlue
Thu, Jan 29 - Sat, Jan 31
JetBlue Logo
2:00 pm - 6:49 pm
STT
-
BOS
5h 49m1 stop
JetBlue Logo
11:55 am - 4:54 pm
BOS
-
STT
3h 59mnonstop
$245JetBlue
Useful Info

Good to know

Low seasonMarch
Cheapest flight$89
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from San Juan Airport to Boston

FAQs for booking flights from Caribbean Islands to Boston

  • How does KAYAK find such low prices on flights from Caribbean Islands to Boston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean Islands to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean Islands to Boston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Boston with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Boston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Caribbean Islands to Boston

 
Need help choosing which airline to fly with from Caribbean Islands to Boston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8025 reviews
7.2Food
7.9Comfort
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

8.0 ExcellentG, Jan 2026
ATL - FLL
Read more Delta reviews

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

On the way my flight entertainment wouldn’t work the screen went black and no matter how many times I tried to turn it on it wouldn’t. Food was surprisingly good but the tray tables were tiny so you couldn’t get anything else on the table. The seats hardly go back and are not overly comfortable. Wouldn’t fly United again.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

In Liberia airport 5 min before our departure the airport was closed for takeoff for 30 min. Upon arrival to IAH we didn’t have any available gate and waited taxing another 40 min. As a result we arrived for 1+ h later. The walkway to the passport control in IAH is about 1-2 ml long. After the passport control you have to pass the security check again. Only 3 out of 16 checkpoints were open and the line was enormously long. As a result, even though we supposed to have 2.5 hrs gap in between the flights we missed our transfer. United rebooked us for the next available flight early morning and provided free hotel and meal vouchers through.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

We had a 2 hour delay that impacted our comanions further travel. I have a feeling AA knows there is a problem at the Cabo airport and does not account for that.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Experience was good. We were delayed in leaving by 15 mins because the flight was waiting on a family that was late in getting to the gate. Food and drink options were as expected. I highly recommend checking in ahead of time using the airline’s app so that it’s quicker to get your luggage tags as soon as you arrive at the terminal. No more waiting in long lines!

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

Our flight was delayed 5 hours, very disorganized, bad communication, confusion. Only good thing was the crew.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

we were delayed because of some safety check that wasn't done or available

Qatar Airways only had spicy meals on the menu in economy class. You might want to get food in the airport before boarding.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

Horrible. I never will travel again with Spirit. Delays and cancellations. Not more words .

Once again, the staff seem to think they are above the customers and treat everyone with disdain, belittling people.

COMMUNICATION!!!! The issue was a crew shortage, which means you knew in advance the issue. Instead of notifying people in advance, we're finding out an hour before the flight it's canceled. You rebooked people to more flights you knew wouldn't get out. You ended by taking part of my party to a completely different state and leaving them there. The next morning, you still have no way to get them to the original destination and they ended up missing an important event. We came out of so much money to check bags multiple times. And on top of all that, the staff in the building seemed to not care and were fairly rude. Overall, just go on and fold and quit making promises to people to get them places when you know you can't. Shoutout to Delta for doing a great job at making it less painful (for those of us who made it).

Flight was canceled 8 hours before departure for lack of operational control and prepositioning of a plane. Then had the audacity to say it was because of weather, however there was no weather here in California or New Orleans or in between. It was the weather in Florida, Florida it had nothing to do with our flight path just the plane was supposed to fly us. 8 hours is more than enough time to move a plane anywhere in the US. That left me with a bill of 1200 dollars to re book a flight oh and kayaks insurance what a joke. Probably will never use kayak or spirit ever again terrible companies terrible customer service. I’ll also let everyone and anyone know this was an abomination and only for the customer. Also will be making a report to the DOT on bad business practices on behalf of kayak and spirit as well as the BBB. Do better, take care of your customers and don’t suck

The flight was cancelled without prior notice. I was inform as I was checking in. No hotel accommodation nor any simple explanation as why it was cancelled.

Terrible. I never made my trip to Puerto Rico and my layover flight from IAH to MCO was delayed over 3 hours and made me miss my connecting flight. I spend 2 days in an airport just to have to go back to Houston. This was a trip for my birthday and I lost money on this trip. I understand the situation with Venezuela affected flights but it’s always something with Spirit.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Flight cancelled and no alternative offered for over a week. Ruined our Christmas vacation plans

Flight was delayed from 10:09pm back to 12:41am and actually took off closer to 1am as they were waiting for an additional flight attendant. Plane was new and crew was fine once we got moving but the delay was rough. Also Spirit (have flown this twice) lands at the satellite gates at BNA and there is a ground shuttle to get you back to the main terminal that adds outdoor elements, extra walking and about 20 min total to the arrival timing. BNA may eventually connect this concourse in a better way as they grow but it’s notable.

The flight was on time, the crew is friendly, and the seat was nice and wide compared to some other airlines. (the KAYAK survey should allow for the response, not applicable, because I did not have any food or take advantage of the entertainment)

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