$116 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 12/6. 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
$179
Overall average: $234
Spirit Airlines
Sat 12/27Wed 1/7
SJU - BOS • Non-stop
Cheapest one-way
$116
Typical prices: $88-$211
Multiple Airlines
Sat 12/6
SJU - BOS • 2 stops
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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, Dec 27 - Wed, Jan 7
Spirit Airlines Logo
3:15 pm - 6:39 pmSJU-BOS
4h 24mnonstop
Spirit Airlines Logo
7:34 pm - 12:41 amBOS-SJU
4h 07mnonstop
$179Spirit Airlines
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Sun, Dec 21 - Fri, Jan 2
Multiple Airlines Logo
6:00 am - 9:23 amSJU-BOS
4h 23mnonstop
Multiple Airlines Logo
7:34 pm - 12:41 amBOS-SJU
4h 07mnonstop
$180Multiple Airlines
Find Deal
Thu, Feb 5 - Wed, Feb 11
Frontier Logo
4:22 pm - 1:13 amSJU-BOS
9h 51m1 stop
Frontier Logo
6:00 am - 3:06 pmBOS-SJU
8h 06m1 stop
$181Frontier
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Thu, Dec 25 - Mon, Jan 5
Frontier Logo
8:00 am - 11:23 amSJU-BOS
4h 23mnonstop
Frontier Logo
8:08 am - 10:15 pmBOS-SJU
13h 07m2 stops
$184Frontier
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Fri, Jan 23 - Sun, Jan 25
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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Mon, Dec 22 - Wed, Dec 31
Delta Logo
1:48 pm - 1:07 amSTT-BOS
12h 19m1 stop
Delta Logo
8:20 am - 1:24 pmBOS-STT
4h 04mnonstop
$239Delta
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Wed, Dec 24 - Tue, Dec 30
American Airlines Logo
4:25 pm - 9:41 amSTT-BOS
18h 16m2 stops
American Airlines Logo
5:59 am - 1:59 pmBOS-STT
7h 00m1 stop
$243American Airlines
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Fri, Dec 12 - Sat, Jan 17
JetBlue Logo
1:50 pm - 11:11 pmMBJ-BOS
9h 21m1 stop
JetBlue Logo
10:45 am - 3:15 pmBOS-MBJ
4h 30mnonstop
$302JetBlue
Find Deal
Fri, Jan 23 - Sun, Jan 25
American Airlines Logo
3:46 pm - 10:56 pmSTT-BOS
8h 10m1 stop
American Airlines Logo
6:45 am - 3:56 pmBOS-STT
8h 11m1 stop
$305American Airlines
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Fri, Dec 5 - Sat, Jan 17
JetBlue Logo
3:05 pm - 11:11 pmMBJ-BOS
8h 06m1 stop
JetBlue Logo
10:45 am - 3:15 pmBOS-MBJ
4h 30mnonstop
$316JetBlue
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Useful Info

Good to know

Low seasonMarch
Cheapest flight$116
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 8002 reviews
7.9Comfort
8.5Crew
7.9Entertainment
8.1Boarding
7.3Food
Airline reviews

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

8.0 ExcellentAnonymous, Nov 2025SFO - MSP
Read more Delta reviews

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

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

the over had ligth did not work'd for the all way

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

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.

flight was good until we arrived at cmh ten minutes early but then sat on tarmac for twenty minutes because a plane was at our gate, so we had to wait despite the pilot tellling us that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

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

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

The flight was on time and the crew was very professional and accommodating. When other airlines are canceling flights Spirit is still flying with on time flights. I have no complaints and will continue to choose Spirit when it is the best option for me.

Very uncomfortable seat. Hard bar under cushion. Flight had no solution except to walk a around at times

Endless, trip oof my life, we still are in in plane waiting for getting off.after 3 hours delay. Not even a glass of water.

The checkin in laguardia was a disaster, scrambling left and right, it was constantly a trying to sell you something, better seat, constantly selling

It was cheap. Spirit is what it is. I got to my destination and home safely. There was no food or entertainment without paying extra, which is fine. That’s why the flight was inexpensive.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

No leg room. My knee was sore for a day.

It was better than expected. But there were two delays in taking off.

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

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!!!

i was unable to check in the flight. refund requested

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