$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 12/18. 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
$124
Typical prices: $112-$265
Spirit Airlines
Sat 2/7Mon 2/9
SJU - BOS • Non-stop
Cheapest one-way
$98
Typical prices: $88-$196
Delta
Thu 12/18
SJU - BOS • 1 stop
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Flight Deals

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

Sat, Feb 7 - Mon, Feb 9
Spirit Airlines Logo
10:52 am - 2:12 pmSJU-BOS
4h 20mnonstop
Spirit Airlines Logo
3:18 pm - 8:24 pmBOS-SJU
4h 06mnonstop
$124Spirit Airlines
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Fri, Jan 23 - Sat, Jan 31
Spirit Airlines Logo
10:52 am - 2:12 pmSJU-BOS
4h 20mnonstop
Spirit Airlines Logo
3:18 pm - 8:24 pmBOS-SJU
4h 06mnonstop
$125Spirit Airlines
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Tue, Dec 23 - Thu, Jan 8
Frontier Logo
8:00 am - 11:23 amSJU-BOS
4h 23mnonstop
Frontier Logo
12:31 pm - 5:30 pmBOS-SJU
3h 59mnonstop
$130Frontier
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Thu, Dec 18 - Mon, Jan 5
Frontier Logo
8:00 am - 11:23 amSJU-BOS
4h 23mnonstop
Frontier Logo
8:08 am - 1:24 amBOS-SJU
16h 16m1 stop
$134Frontier
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Mon, Jan 26 - Fri, Jan 30
Delta Logo
2:32 pm - 5:53 pmSTT-BOS
4h 21mnonstop
Delta Logo
8:55 am - 2:00 pmBOS-STT
4h 05mnonstop
$234Delta
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Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
12:22 pm - 8:03 pmPOS-BOS
8h 41m1 stop
JetBlue Logo
8:15 pm - 7:17 amBOS-POS
10h 02m1 stop
$238JetBlue
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Mon, Jan 26 - Thu, Jan 29
Delta Logo
2:32 pm - 5:53 pmSTT-BOS
4h 21mnonstop
Delta Logo
5:35 am - 3:05 pmBOS-STT
8h 30m1 stop
$239Delta
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Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
12:22 pm - 8:03 pmPOS-BOS
8h 41m1 stop
JetBlue Logo
8:15 pm - 7:17 amBOS-POS
10h 02m1 stop
$248JetBlue
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Fri, Feb 13 - Sat, Feb 21
American Airlines Logo
4:40 pm - 10:09 amPOS-BOS
18h 29m2 stops
American Airlines Logo
5:10 pm - 3:39 pmBOS-POS
21h 29m2 stops
$291American Airlines
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Tue, Dec 16 - Sat, Jan 3
American Airlines Logo
11:13 am - 8:56 pmMBJ-BOS
9h 43m1 stop
American Airlines Logo
6:48 pm - 12:07 pmBOS-MBJ
17h 19m1 stop
$325American Airlines
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Good to know

Low seasonMarch
Cheapest flight$98
Best time to beat the crowds with an average 5% 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 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 8010 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.3Food
7.9Entertainment
Airline reviews

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

6.0 GoodMary Heather, Nov 2025LGA - MKE
Read more Delta reviews

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

One of the best airlines that I flew on, the flight attendants were very attentive and professional.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

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

My flight was delayed about three hours. I got home at 3:30 in the morning very bad experience.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

I like how the crew and pilot kept us updated Even though our flight was slightly delayed. We made up time for it in the air. I really did enjoy my seat and amenities and my trip and value overall.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

The inflight staff is never the issue always the extra and charges american charges! Literally 30 bucks for WiFi! Is insane and then it’s choppy and slow. If you pay for it once you don’t need to pay again for switching aircraft especially when there is flight delays

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

We were told the flight was delayed 5 times, then it was moved to the next day.

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.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

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

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

Excellent! No complaints! All the staff from the counter to the airplane crew, was just amazing and pleasing to talk to

My baby was crying uncontrollably for the longest time and the entire crew was SO supportive, I’m so appreciative of them. Thank you so much for the support during an exhausting moment. We got very lucky.

I didn't eat, so I can't rate the food. Delayed set off was beyond

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

I hope you continue to be one of the great company

Crew are always very angry and dismissive like they seem they are being forced to work. In addition, there was a long line for the bathrooms, and only one was allowed to be used. No reason was given for only one bathroom being available; apparently, the stewardess was more interested in using the jumpseat instead of allowing the customers to use the bathroom.

Very positive in both directions. Safe travels, nice staff, lost and found in fact found my phone under my chair! I was out of cash after my NYC trip otherwise I would've offered a reward for helping my day out immensly! Thanks you so much Spirit staff!

I stopped flying spirit as much because they are crooks and thieves. It's not like other airlines where you can at least get credits they just take your money.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

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