$98 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 5/23. 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

Sat, Apr 11 - Sun, Apr 12
Multiple Airlines Logo
10:00 am - 2:18 pm
SJU
-
BOS
4h 18mnonstop
Multiple Airlines Logo
11:18 am - 3:17 pm
BOS
-
SJU
3h 59mnonstop
$159Multiple Airlines
Fri, Apr 10 - Sun, Apr 12
Multiple Airlines Logo
1:45 am - 9:54 am
SJU
-
BOS
8h 09m
1 stop
Multiple Airlines Logo
11:18 am - 3:17 pm
BOS
-
SJU
3h 59mnonstop
$168Multiple Airlines
Sat, Apr 11 - Mon, Apr 13
Spirit Airlines Logo
10:00 am - 2:18 pm
SJU
-
BOS
4h 18mnonstop
Spirit Airlines Logo
3:23 pm - 7:19 pm
BOS
-
SJU
3h 56mnonstop
$174Spirit Airlines
Sat, Apr 11 - Sun, Apr 26
Spirit Airlines Logo
10:00 am - 2:18 pm
SJU
-
BOS
4h 18mnonstop
Spirit Airlines Logo
2:12 pm - 6:06 pm
BOS
-
SJU
3h 54mnonstop
$179Spirit Airlines
Thu, Apr 30 - Wed, May 13
JetBlue Logo
5:38 pm - 7:40 am
POS
-
BOS
14h 02m
1 stop
JetBlue Logo
5:20 am - 1:36 pm
BOS
-
POS
8h 16m
1 stop
$318JetBlue
Thu, Apr 30 - Sun, May 10
American Airlines Logo
4:38 pm - 11:04 am
BGI
-
BOS
18h 26m
1 stop
American Airlines Logo
5:00 am - 9:16 pm
BOS
-
BGI
16h 16m
1 stop
$324American Airlines
Tue, May 19 - Tue, May 26
American Airlines Logo
8:00 am - 11:35 pm
BGI
-
BOS
15h 35m
2 stops
American Airlines Logo
8:00 am - 9:36 pm
BOS
-
BGI
13h 36m
2 stops
$329American Airlines
Fri, May 1 - Sun, May 10
JetBlue Logo
5:38 pm - 7:10 am
POS
-
BOS
13h 32m
1 stop
JetBlue Logo
5:20 am - 1:36 pm
BOS
-
POS
8h 16m
1 stop
$338JetBlue
Tue, May 5 - Tue, Sep 8
Delta Logo
6:00 am - 3:28 pm
STI
-
BOS
9h 28m
1 stop
Delta Logo
6:00 am - 12:43 pm
BOS
-
STI
6h 43m
1 stop
$349Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
3:15 pm - 6:51 pm
NAS
-
BOS
3h 36mnonstop
Delta Logo
7:00 am - 2:50 pm
BOS
-
NAS
7h 50m
1 stop
$351Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$98
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 8386 reviews
7.9Comfort
8.5Crew
7.2Food
8.1Boarding
7.8Entertainment
Airline reviews

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

10.0 ExcellentSarah, Apr 2026
LAX - SFO
Read more Delta reviews

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

For the price point it was very good. Definitely leave on the earlier flights as it can become terribly crowded later in the day

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Delayed our flight to accommodate another flight but didn’t make the decision to do so until we were supposed to board despite having all the same information hours prior. Arrived so delayed that we didn’t get a gate and had to deplane on the tarmac and get bussed to terminal in the rain after 1am. Arrived to the terminal and due to construction could not get a ride share - had to either take the air train to Howard beach or stand in line with 200 other people waiting for a taxi.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Buying ticket from kayak instant booking was a huge mistake, never to be repeated again! The Kayak didn’t book the tickets directly, it handed it off to a third party Underpricer, that booked a code shared American Airlines flight operated by Cathay Pacific!! When managing the booking American Airlines would recognize the itinerary but wouldn’t let me do anything stating, the flight is operated by Cathay Pacific so go to their website. Cathay Pacific would recognize the itinerary, neither by reservation ID or ticket number…asking to reach out to the third party Underpricer….calling Underpricer resulted in no help like seat requests, mileage number or upgrade request, 15hr layover accommodation voucher guidance…so net in net avoid booking through three layers of intermediaries

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

A chaotic and uncomfortable experience from start to finish. The boarding process was a disaster; despite group numbers, it was a free-for-all that the staff failed to manage (especially after group 5). Once on board, the "entertainment" was non-existent. There are no seatback screens, and the mobile app selection is incredibly thin. The hardware is severely dated. My seat had zero cushioning left—it felt like sitting on a hard board for the entire flight—and the legroom was cramped. To make matters worse, the bathroom was repulsive, with toilet paper, soiled paper towels and liquid/pee all over the floor. When I did interact with the crew, they provided the absolute bare minimum and made me feel like an inconvenience for asking for anything. Avoid this flight if you can.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

It was canceled at the last minute. While I was literally at the airport. Messed my entire trip up.

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

Landing was technically perfect. What I didn't like is the pricey internet. Both flights with excellent crews. I'm 6 feet 210 pounds and could easily fit in the chair.

Long long delay, no AC while delayed, gate changes, just for the most uncomfortable flight of your life.

Everything was smooth sailing. Great crew, easy flight and was surprised with an upgraded seat. Thank you all!

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

I truly admired that the last minute flight attendants were willing to come to serve flight # 1465 and think they should be extra compensated. Doesn't have to beonetary a star a permanent position with Spirit as long as she flies etc. They were o so pleasant and accommodating. 😊😊. Please also serve water. Plain unadulterated water 💧! Invest in a filter of your own the cost of bottles are a penny on the dollar and you could have a plug on advertising with labeling. This could be hilarious "WATER TO REFREST THE SPIRIT FROM SPIRIT ITSELF!" - Free idea!😄😄😄. Anyway overall, though a tad late the flight met expectations. Thanks you Spirit, for everything.

We were delayed and the bag charge fees are very expensive.

The worst. My flight was canceled :-- by email! -- at 10pm, just 8 hours prior to departure. Normally, given the early departure time, I would've been asleep. I was lucky to be awake and to be able to take action. Even worse, it turns out that the flight wasn't canceled (confirmed because I was at the airport and saw it loading), Spirit just canceled my reservation, probably because I got such a good rate! Utterly appalling. Notably, Spirit did not inform you (Kayak) of the change, so I kept getting alerts from you.

It was my first time flying with spirit. It was amazing. I loved it.

Horrible airline .. my flight was cancel , the only offer to flight next day was no good for me , representative from spirit advise everybody to buy the new ticket from southwest airline and spirit will pay back the money we spend on new ticket but after we did this they don’t want to pay us back , .. customer service is not help anybody Chat text messages it is horrible also , robots can’t answer and help u with anything … I send the complains to head quarter in Miami and department of transportation

The ticket price are reasonable, however, they can do better with the price on the luggage. Overall, I will continue using spirit.

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