$98 Find Cheap Flights from Caribbean 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 5/22. 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 to Boston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean 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 to Boston

Fri, May 8 - Tue, May 12
Frontier Logo
5:15 pm - 1:24 am
SJU
-
BOS
8h 09m
1 stop
Frontier Logo
10:07 am - 2:08 am
BOS
-
SJU
16h 01m
1 stop
$176Frontier
Thu, May 7 - Wed, May 13
Frontier Logo
5:15 pm - 7:49 am
SJU
-
BOS
14h 34m
1 stop
Frontier Logo
10:07 am - 2:08 am
BOS
-
SJU
16h 01m
1 stop
$186Frontier
Mon, Apr 20 - Wed, Apr 22
Spirit Airlines Logo
2:59 am - 10:29 am
SJU
-
BOS
7h 30m
1 stop
Spirit Airlines Logo
11:20 am - 12:58 am
BOS
-
SJU
13h 38m
1 stop
$187Spirit Airlines
Sat, Apr 18 - Wed, Apr 22
Spirit Airlines Logo
10:25 am - 2:32 pm
SJU
-
BOS
4h 07mnonstop
Spirit Airlines Logo
11:20 am - 12:58 am
BOS
-
SJU
13h 38m
1 stop
$195Spirit Airlines
Thu, Apr 16 - Wed, Apr 22
Delta Logo
2:33 pm - 6:59 pm
STT
-
BOS
4h 26mnonstop
Delta Logo
8:45 am - 12:42 pm
BOS
-
STT
3h 57mnonstop
$201Delta
Thu, Apr 16 - Wed, Apr 22
Delta Logo
2:33 pm - 6:59 pm
STT
-
BOS
4h 26mnonstop
Delta Logo
6:00 am - 1:13 pm
BOS
-
STT
7h 13m
1 stop
$206Delta
Thu, Apr 16 - Wed, Apr 22
American Airlines Logo
12:25 pm - 11:30 pm
STT
-
BOS
11h 05m
2 stops
American Airlines Logo
6:00 am - 12:35 pm
BOS
-
STT
6h 35m
1 stop
$285American Airlines
Thu, Apr 16 - Mon, Apr 20
American Airlines Logo
3:29 pm - 11:52 pm
STT
-
BOS
8h 23m
1 stop
American Airlines Logo
6:53 pm - 12:07 pm
BOS
-
STT
17h 14m
1 stop
$300American Airlines
Sat, Apr 18 - Sat, Apr 25
JetBlue Logo
11:39 am - 2:59 pm
NAS
-
BOS
3h 20mnonstop
JetBlue Logo
11:41 am - 3:09 pm
BOS
-
NAS
3h 28mnonstop
$346JetBlue
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
$359JetBlue
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 8% lower on average.
Flight from San Juan Airport to Boston

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

Insights shared by verified travelers who flew the route from Caribbean 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 to Boston

  • How does KAYAK find such low prices on flights from Caribbean 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 to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Caribbean 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean 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 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 to Boston

 
Need help choosing which airline to fly with from Caribbean 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 8374 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

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.

6.0 GoodJoseph, Apr 2026
MSP - RIC
Read more Delta reviews

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.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Our recent international travel was from Newark, NJ to Grenada via Atlanta. During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta as it did not wait for arriving passengers. Consequently, we were delayed by 24 hours before the next available flight was provided. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for me as a resident of New Jersey.

This was my first flight with Delta, the overall experience was good. I would definitely consider them more with my future flights.

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.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Early morning flight and no food in First Class except a "salmon" box. No thank you. Was informed before take off by Captain that the plane was not serviced before we boarded in Phoenix. How does that happen? Need more frequent additions/turn over on the Entertainment. Thanks

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Delayed 24 hours. Should have called it much earlier They provided quality accommodations, food vouchers etc. FINALLY The issues started at 8 AM and they cancelled the flight at 11:30 PM, with no plans for a new flight.

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

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

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.

That this is my second time the they cancel flights and they always wait until the last minute to let people know

The flight was supposed to leave at 6:22pm we are just now leaving the gate after deplaning twice at 1:07am.

Spirit is always late. Every single time. Always a different reason

They keep delaying and cancel at last moment and height was for you to get refund need to be in chat line for two hours. I complained to DOT. Never recommend this airline on Kayak please

First flight in along time with spirit! I’m honored to say this flight was excellent 😊

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Every connection was late but that meant I was not running from one to the next so that was a good thing. No one wants to miss a connection

Food and entertainment see irrelevant to rate them as that’s not really an option anymore. The flight was fast and friendly. The plane was immaculately clean.

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