$115 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 6/4. 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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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

Fri, Aug 14 - Thu, Aug 20
Frontier Logo
5:15 pm - 1:23 am
SJU
-
BOS
8h 08m
1 stop
Frontier Logo
6:00 am - 2:15 pm
BOS
-
SJU
8h 15m
1 stop
$255Frontier
Fri, Aug 14 - Thu, Aug 20
Frontier Logo
5:15 pm - 1:23 am
SJU
-
BOS
8h 08m
1 stop
Frontier Logo
6:00 am - 2:15 pm
BOS
-
SJU
8h 15m
1 stop
$260Frontier
Fri, Oct 30 - Fri, Nov 6
Arajet Logo
6:30 am - 10:45 am
SDQ
-
BOS
4h 15mnonstop
Arajet Logo
11:15 am - 4:30 pm
BOS
-
SDQ
4h 15mnonstop
$310Arajet
Fri, Sep 18 - Sun, Sep 27
Arajet Logo
6:30 am - 10:45 am
SDQ
-
BOS
4h 15mnonstop
Arajet Logo
10:20 pm - 2:35 am
BOS
-
SDQ
4h 15mnonstop
$319Arajet
Thu, Jun 4 - Wed, Jun 10
JetBlue Logo
4:30 pm - 9:29 pm
AUA
-
BOS
4h 59mnonstop
JetBlue Logo
10:20 am - 3:10 pm
BOS
-
AUA
4h 50mnonstop
$357JetBlue
Thu, Jun 4 - Wed, Jun 10
JetBlue Logo
1:50 pm - 6:45 pm
AUA
-
BOS
4h 55mnonstop
JetBlue Logo
10:20 am - 3:10 pm
BOS
-
AUA
4h 50mnonstop
$358JetBlue
Fri, May 29 - Tue, Jun 2
American Airlines Logo
5:17 pm - 10:06 am
MBJ
-
BOS
15h 49m
1 stop
American Airlines Logo
8:00 am - 1:55 pm
BOS
-
MBJ
6h 55m
1 stop
$366American Airlines
Mon, Jul 20 - Sun, Aug 2
American Airlines Logo
4:50 pm - 10:16 am
STT
-
BOS
17h 26m
1 stop
American Airlines Logo
6:04 am - 1:48 pm
BOS
-
STT
7h 44m
1 stop
$370American Airlines
Sat, Jun 27 - Fri, Jul 10
Delta Logo
1:55 pm - 10:41 pm
AUA
-
BOS
8h 46m
1 stop
Delta Logo
8:40 pm - 12:16 pm
BOS
-
AUA
15h 36m
1 stop
$372Delta
Sat, Sep 26 - Sat, Oct 3
Delta Logo
8:40 pm - 7:22 am
STI
-
BOS
10h 42m
1 stop
Delta Logo
6:00 am - 7:11 pm
BOS
-
STI
13h 11m
1 stop
$434Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$115
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from San Juan Airport 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.
7.9
DeltaOverall score based on 8455 reviews
7.2Food
8.1Boarding
7.8Comfort
7.8Entertainment
8.5Crew
Airline reviews

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

10.0 ExcellentCharles, May 2026
DTW - DEN
Read more Delta reviews

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

Much better than I expected. I had an economy ticket so I was really happy the flight was so comfy and the service so generous. Passengers were all polite too.

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

It took so long to do a baggage drop and it was bad enough. I had to go to the extreme end of the terminal because it’s a USA flight and go all the way back to the center indigo to security.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

Every flight was delayed except the last one. One layover turned into two. Travel time extended by three hours. No compensation offered. Repeatedly asked if I'd like to cancel my flight for a partial refund.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

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

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

The small flights with Valet Luggage has a poor service

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

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

There was no flight. Spirit went bankrupt Right before my departure and kayak did not refund me any money. I would like my refund kayak. How can I get it? Please let me know. Thank you

Flights were canceled due to airline shutting down and haven’t received a reimbursement. Had to book last minute new flights which were expensive

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Had a flight change had to get a credit.will I get my money back.

Shut down without prior notice End up with spending lots of extra $$$

There was a crack in my window seal. And Spirit is now closed forever.

The company went out of business and now I'm stuck in Ft. Lauderdale. Would not recommend.

Spirit changed flight times by 12 hours with coming and going so I refunded tickets and drove

The airline cancel mi flight, lost a lot of money!!!

They closed the doors earlier than posted. I missed my flight with a slim 5 minutes bc they closed the doors earlier than earlier. My luggage never made it onto the flight and I had to find a new flight to Dallas bc the only option they could rebook me on was for leaving miami.

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