$105 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 5/14. 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

Sat, May 16 - Mon, May 18
Frontier Logo
5:15 pm - 1:24 am
SJU
-
BOS
8h 09m
1 stop
Frontier Logo
10:17 am - 2:08 am
BOS
-
SJU
15h 51m
1 stop
$186Frontier
Sat, May 16 - Tue, May 19
Frontier Logo
5:15 pm - 1:24 am
SJU
-
BOS
8h 09m
1 stop
Frontier Logo
10:07 am - 10:43 pm
BOS
-
SJU
12h 36m
1 stop
$194Frontier
Fri, May 22 - Sun, May 24
Arajet Logo
6:30 am - 10:45 am
SDQ
-
BOS
4h 15mnonstop
Arajet Logo
10:20 pm - 2:35 am
BOS
-
SDQ
4h 15mnonstop
$288Arajet
Fri, Sep 18 - Wed, Oct 7
Arajet Logo
6:30 am - 10:45 am
SDQ
-
BOS
4h 15mnonstop
Arajet Logo
12:15 pm - 4:30 pm
BOS
-
SDQ
4h 15mnonstop
$300Arajet
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
3:29 pm - 12:40 am
BGI
-
BOS
9h 11m
1 stop
American Airlines Logo
5:01 am - 9:35 pm
BOS
-
BGI
16h 34m
1 stop
$330American Airlines
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
3:58 pm - 7:39 am
BGI
-
BOS
15h 41m
2 stops
American Airlines Logo
8:00 am - 9:35 pm
BOS
-
BGI
13h 35m
1 stop
$334American Airlines
Sun, May 17 - Sun, May 24
JetBlue Logo
1:50 pm - 6:45 pm
AUA
-
BOS
4h 55mnonstop
JetBlue Logo
11:55 am - 4:46 pm
BOS
-
AUA
4h 51mnonstop
$335JetBlue
Wed, Sep 23 - Wed, Sep 30
JetBlue Logo
2:20 pm - 9:50 pm
BQN
-
BOS
7h 30m
1 stop
JetBlue Logo
1:00 pm - 10:39 pm
BOS
-
BQN
9h 39m
1 stop
$356JetBlue
Thu, May 21 - Wed, May 27
Delta Logo
1:55 pm - 11:37 pm
AUA
-
BOS
9h 42m
1 stop
Delta Logo
5:35 am - 2:10 pm
BOS
-
AUA
8h 35m
1 stop
$372Delta
Thu, May 21 - Tue, May 26
Delta Logo
8:59 pm - 7:22 am
STI
-
BOS
10h 23m
1 stop
Delta Logo
6:00 am - 12:23 pm
BOS
-
STI
6h 23m
1 stop
$403Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$105
Best time to beat the crowds but there is an average 3% 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 8464 reviews
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
8.5Crew
Airline reviews

Round trip flight to Canada and back to the US was smooth and efficient.

8.0 ExcellentBrent, Apr 2026
YWG - MSP
Read more Delta reviews

Round trip flight to Canada and back to the US was smooth and efficient.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

Spanish speaker flight attendants were incredibly rude. A male flight attendant named Allen, grabbed my bag out of the overhead bin and moved it without my permission. When I asked what he was doing, he informed me that the overhead bins were public space? It would be easy to ignore this comment, as you don’t know the whole story, but the flight attendants were militant and rude. Delta, you can do better!

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

My business class seat was inoperable and unable to recline for 10 hour flight.

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.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

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

Not having an assigned seat until boarding and then having to check my bag.

Boarding was done extremely poorly, with huge crowds gate loiterers blocking people from boarding, multiple lines of people trying to merge into one line. One of the male flight attendants who was doing drink service was not happy about having to let a passenger back to their seat and was unnecessarily sassy about it. I thought he was pretty entitled and not a great ambassador for JetBlue

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

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

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Flight was smooth, amenities (entertainment options and power outlets) were good, sears decent)

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

Poor... food was horrible, boarding very slow, service on board mediocre

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

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

The agent cancel my flight without my consent. So the situation generate me a lot of troubles, specially because we were traveling with a baby

Wonderful! Very polite crew that was dedicated to excellent customer service

Everyone was nice but it's budget. There's nothing free and no entertainment

The flight was delayed for over an hour. No one at the gate said anything about the flight being delayed. I had to rely on my phone for updates. Absolutely no communication at the gate.

The AC broke and we were onboard for 2 hrs waiting for them to fix it. It was so hot and we could not get any water or anything to drink. They finally let us off the plane after the second attempt and we boarded a new plane. We didn't land till 12:15am!

The boarding process was simple but the seats were very uncomfortable. The staff lady was also very hard to understand when she spoke over the intercom about procedures and updates. Other staff members seemed like they were just tired and didnt want to be on the plane. Im used to happy attendants and being able to understand what is said over the speakers.

The seats on this aircraft were so uncomfortable it was like sitting on high school gym bleachers. I’m not sure we will fly spirit again. I also paid for the so called shortcut security and ended up being told to get in the regular security line, don’t waste your money.

There was no flight. Call the airline and confirmed. I have no idea why you think that I flew on the days that you say I did.

They canceled my flight and never told me. There was no follow up email. I had to buy another ticket the day of.

Easy to get our TSA pre check #added. Flight crew was great and entertaining and we landed early!

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