$152 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 9/17. 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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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

Fri, Oct 2 - Sun, Oct 18
Arajet Logo
6:30 am - 10:45 am
SDQ
-
BOS
4h 15mnonstop
Arajet Logo
10:20 pm - 2:35 am
BOS
-
SDQ
4h 15mnonstop
$215Arajet
Thu, Oct 1 - Thu, Oct 8
Arajet Logo
4:35 pm - 8:50 pm
SDQ
-
BOS
4h 15mnonstop
Arajet Logo
10:20 pm - 2:35 am
BOS
-
SDQ
4h 15mnonstop
$228Arajet
Wed, Oct 7 - Wed, Oct 14
JetBlue Logo
4:30 pm - 11:35 pm
SJU
-
BOS
7h 05m
1 stop
JetBlue Logo
7:20 pm - 11:58 pm
BOS
-
SJU
4h 38mnonstop
$301JetBlue
Thu, Aug 13 - Sun, Aug 16
JetBlue Logo
7:45 pm - 11:50 pm
SJU
-
BOS
4h 05mnonstop
JetBlue Logo
7:50 pm - 11:54 pm
BOS
-
SJU
4h 04mnonstop
$308JetBlue
Fri, Sep 4 - Mon, Sep 7
Delta Logo
2:10 pm - 6:21 pm
SJU
-
BOS
4h 11mnonstop
Delta Logo
8:50 am - 12:57 pm
BOS
-
SJU
4h 07mnonstop
$323Delta
Thu, Sep 24 - Sat, Oct 3
Delta Logo
7:30 am - 2:42 pm
SJU
-
BOS
7h 12m
1 stop
Delta Logo
8:55 am - 12:57 pm
BOS
-
SJU
4h 02mnonstop
$328Delta
Sat, Jul 4 - Fri, Sep 4
United Airlines Logo
4:33 pm - 11:19 pm
MBJ
-
BOS
29h 46m
1 stop
United Airlines Logo
5:45 am - 1:30 pm
BOS
-
MBJ
32h 45m
2 stops
$382United Airlines
Sat, Jul 4 - Fri, Sep 4
American Airlines Logo
3:02 pm - 8:31 am
MBJ
-
BOS
16h 29m
1 stop
American Airlines Logo
6:14 am - 1:12 pm
BOS
-
MBJ
7h 58m
1 stop
$386American Airlines
Sat, Oct 3 - Tue, Oct 6
American Airlines Logo
1:41 pm - 8:33 am
STT
-
BOS
18h 52m
2 stops
American Airlines Logo
7:21 pm - 12:40 pm
BOS
-
STT
17h 19m
2 stops
$390American Airlines
Thu, Jul 16 - Wed, Jul 22
United Airlines Logo
2:00 am - 11:59 pm
POS
-
BOS
21h 59m
2 stops
United Airlines Logo
6:00 am - 12:50 am
BOS
-
POS
18h 50m
2 stops
$390United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$152
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Punta Cana to Boston

Flights from Caribbean Islands to Boston: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Caribbean Islands to Boston 
JasmaryFlew with Spirit Airlines
SJU
-
BOS
Feb 2026
I would advice passengers to bring their own snack as most items are out of stock
slovely08Flew with JetBlue
AUA
-
BOS
Dec 2024
Be prepared for long security times, you have to clear customs in Aruba, and there can be a substantial line if you get there at the wrong time. They tell you to be there 3 hours early for a reason.

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.
7.8
DeltaOverall score based on 8424 reviews
7.8Entertainment
7.8Comfort
8.1Boarding
7.2Food
8.5Crew
Airline reviews

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

10.0 ExcellentAnonymous, Jun 2026
SEA - LAX
Read more Delta reviews

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

Flight attendants were great. Food mediocre. Bamboo utensils not Great especially if you have to cut something. Seating a bit crowded.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

The crew was the worst ive ever had in my life flying with United Airlines, letting another person move my bag without asking and then the staff saying would the floor be better after I kept begging saying dont move my bag it has fragile things inside. This incident truly makes me they favor other customers more and I dont want to worry about being on the tail end. Especially if they dont listen any input, no care for what I asked but accommodated those who are reckless and disturb others more...

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

United has been holding my money for a cancel on another ticket they wouldn’t let me fly for going on 5 months. Terrible service I wouldn’t choose to buy tickets or fly with united again. Very bad experience generally dishonorable and poor service .

The seats were very nice in premium economy. The service was good. The flight was slightly bumpy. Would have appreciated more updates from the pilots.

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Checking bag at terminal was horrible. No agents to check us in and only 1 kiosk working. Boarding went ok. Crew onboard was very scattered rained. Missed our row while serving and then didn’t see them hardly again.

Maybe focus more on delivering a good product vs selling me a damn credit card

American Airlines is a great dependable airline, on time arrival and departure with polite crew and staff.

I think since I am an AA Advantage member, my checked bags should have been free, but I paid for all 4 of us.

This flight moved Gates several times in a short time period, from B to C, which required a substantial walk or rail ride. Then the flight was delayed more than 2 hours and the food was subpar compared to other flights.

Flight was delayed multiple times without giving any particular reason and the only thing that was communicated was that 'Aircraft is getting ready'. I was stuck at SFO airport for 15 hours and finally took Southwest Airlines flight back home to Dallas.

Rudest flight attendants ever, waited over 20 for light to be answered and it never was then tried to flag down an attendant who said someone else would come, just needed water to take some medicine Food bad

I had the best flight crew I have ever experienced in all my years flying with AA. I would specially like to thank Till Tatum/96038 for her kindness professionalism and outstanding service! My son turned 8 years old one day before our flight and she went out of her way to make him feel so special. We will never forget this flight! The whole crew made a special card for Frankie’s bday and it really touched our hearts. He will never forget it and neither will we! Thank you with all our hearts! We hope to be on more flights with Till Tatum and this amazing crew.

Hydraulic leak caused the flight to be cancelled. Auto system scheduled us on a 3 am flight. Wevhsedvrebook on the app and hit schedules later in the afternoon. Our luggage per gate and ticket agent would be rescanned and put in our new flight. Did not happen. Our luggage stayed in hsv. Baggage claim in wash dc unable to help. We filed a claim. Several emails about our luggage were in conflict with one another. Called as baggage and was on hold 30 minutes. Oscar said one of 2 was out fir delivery then cancelled. About 45 minutes later both pieces were delivered. Their system is suspect

My entertainment unit kept locking up and had to be restarted multiple times. Also those commercials for Budapest and Ralph Laureen. Come on those were stuff only those who can afford the outrageous fees of first and business class would be interested in.. And the fact you have no military discount is not good either,

I was not clear if food was offered or not.

For whatever reason, I could not check in online. Kept getting the "It's not you it's us" message. Even when we tried the kiosk at the airport - same results. The check-in person had a very difficult time getting our boarding passes together despite the fact that we could show confirmation on the jetblue website. After a very long time we finally got boarding passes. The only other issue is, my vegetarian meal featured chicken.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

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