$116 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 12/13. 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
$210
Typical prices: $497-$586
Spirit Airlines
Sat 12/13Tue 12/16
AUA - BOS • 1 stop
Cheapest non-stop
$234
Delta
Thu 12/25Fri 1/2
STT - BOS • Non-stop
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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

Sat, Dec 13 - Tue, Dec 16
Spirit Airlines Logo
4:40 pm - 11:56 pmAUA-BOS
8h 16m1 stop
Spirit Airlines Logo
5:45 am - 3:35 pmBOS-AUA
8h 50m1 stop
$210Spirit Airlines
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Sat, Dec 20 - Thu, Jan 1
Frontier Logo
9:58 pm - 10:41 amSJU-BOS
13h 43m1 stop
Frontier Logo
12:18 pm - 5:22 pmBOS-SJU
4h 04mnonstop
$225Frontier
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Thu, Mar 5 - Mon, Mar 9
Delta Logo
4:26 pm - 7:33 amSXM-BOS
16h 07m1 stop
Delta Logo
8:45 pm - 11:15 amBOS-SXM
14h 30m1 stop
$229Delta
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Thu, Dec 25 - Fri, Jan 2
Delta Logo
2:34 pm - 5:56 pmSTT-BOS
4h 22mnonstop
Delta Logo
8:20 am - 1:24 pmBOS-STT
4h 04mnonstop
$234Delta
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Thu, Dec 25 - Fri, Jan 2
United Airlines Logo
5:20 pm - 11:54 pmSTT-BOS
7h 34m1 stop
United Airlines Logo
6:01 am - 4:18 pmBOS-STT
9h 17m1 stop
$243United Airlines
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Wed, Dec 17 - Sat, Jan 3
American Airlines Logo
5:25 pm - 12:08 pmSXM-BOS
19h 43m2 stops
American Airlines Logo
7:00 pm - 1:59 pmBOS-SXM
17h 59m2 stops
$256American Airlines
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Sat, Dec 6 - Wed, Dec 10
American Airlines Logo
3:31 pm - 10:43 pmSXM-BOS
8h 12m1 stop
American Airlines Logo
6:29 am - 4:25 pmBOS-SXM
8h 56m1 stop
$278American Airlines
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Tue, Mar 10 - Thu, Mar 19
JetBlue Logo
1:01 pm - 6:53 pmSTT-BOS
5h 52m1 stop
JetBlue Logo
9:45 am - 1:46 pmBOS-STT
4h 01mnonstop
$292JetBlue
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Wed, Feb 18 - Sun, Feb 22
JetBlue Logo
3:56 pm - 11:32 pmSTT-BOS
8h 36m1 stop
JetBlue Logo
8:00 am - 1:06 pmBOS-STT
4h 06mnonstop
$314JetBlue
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Thu, Feb 5 - Mon, Feb 9
United Airlines Logo
6:00 am - 1:13 pmSTI-BOS
8h 13m1 stop
United Airlines Logo
9:30 am - 11:51 pmBOS-STI
13h 21m2 stops
$363United Airlines
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Good to know

Low seasonMarch
Cheapest flight$116
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 12% 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 8008 reviews
8.5Crew
7.9Comfort
7.3Food
8.1Boarding
7.9Entertainment
Airline reviews

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

8.0 ExcellentAnonymous, Nov 2025SFO - MSP
Read more Delta reviews

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

the over had ligth did not work'd for the all way

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

United has come a long way, it’s been a fantastic experience traveling with them.

Even though we were delayed, we were able to make our connection

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Great crew, excellent landing, good food. Over all great experience. Thank you!

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

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.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

Endless, trip oof my life, we still are in in plane waiting for getting off.after 3 hours delay. Not even a glass of water.

The checkin in laguardia was a disaster, scrambling left and right, it was constantly a trying to sell you something, better seat, constantly selling

It was cheap. Spirit is what it is. I got to my destination and home safely. There was no food or entertainment without paying extra, which is fine. That’s why the flight was inexpensive.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

No leg room. My knee was sore for a day.

It was better than expected. But there were two delays in taking off.

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

Flight was delayed. (To be excepted because of TSA shortage) I’m super short and still struggled with leg room, there was no screen, and the seat didn’t recline at all.

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