Find cheap flights from Caribbean to Boston from $59
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 10/25. 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.Round-trip
1 adult
Economy
Sat 10/21
Sat 10/28
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Good to know
FAQs for booking flights from Caribbean to Boston
Which airlines have a flexible cancellation policy for flights from Caribbean to Boston due to COVID-19?
JetBlue, TAP AIR PORTUGAL and Aer Lingus have all waived their change and cancellation fees on flights from Caribbean to Boston. Confirm policies on booking site.
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.
Top 5 airlines serving from Caribbean to Boston
8.1
JetBlueOverall score based on 19464 reviews
86crew
78food
83boarding
79entertainment
82overall
82comfort
Airline reviews
Pros: "Friendly attendant helped me get seats with my daughter together. Everyone was very nice and polite."
Cons: "Everything was great for this trip"
Pros: "Friendly attendant helped me get seats with my daughter together. Everyone was very nice and polite."
Cons: "Everything was great for this trip"
Pros: "Jet blue flights seem generally good. Like the WiFi access to be Able to use flight time efficiently."
Pros: "The available movies were pretty good."
Cons: "The crew member serving the food was way too slow."
Cons: "Flight was 3 1/2 hours delayed. In-flight entertainment system didn’t function. They didn’t perform a beverage/snack service. Very poor overall. Disappointing."
Cons: "Our flight was delayed 4 times. We then sat on the runway for an extra 45 minutes because someone’s tv did not work. We missed our set transportation which was already rescheduled 4 times and had to pay $150 Uber to get home"
Cons: "They had to reset entertainment sets 3 times before they started working. This happens regularly on the SFO to BOS jetblue flight."
Cons: "We had a delay of 3 hrs which kept us waiting in the middle of the night"
Pros: "There was actual room for my legs."
Cons: "There could have been more legroom so that you could actually get out without almost sitting in someone else's lap. But it was easier than my last flight (on American Airlines). Having a meal available would have been nice on a flight of almost 6 hours."
Cons: "Entertainment screen in our section of the plane were not functioning correctly. The crew made several attempts to reset the screens but it didn't work,"
Pros: "Great crew and service"
Cons: "The delay was longgg but I know that couldn’t be avoided"
Pros: "Nice plane, good service and pilots, great landing - no issues at all."
Cons: "Flight attendant in First class was visibly frustrated and unfriendly. He was not helping with my simple request for a blanket. Also, the were no food service in first class."
Pros: "individual TVs"
Cons: "it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off."
Cons: "Flight was 1,5 hr delayed, which almost caused me to miss my connecting flight"
Cons: "Wheelchair shortage on arrival, although I had one reserved. Waited for a while then walked. Not ideal. Very long wait for bus to rental car center."
Cons: "We thought we were flying AirFrance as our emails came from them and were surprised to learn after waiting in the AirFrance baggage drop queue for 30 mins that we were in the wrong place."
Cons: "Double booking and payment of flight. Dropped flight bookings. Not a good trip"
Cons: "the inefficiency and extra steps required to travel. Quite lacking in smooth transition between flights, significantly below expectations relative to other airlines"
Pros: "In-flight entertainment and communication."
Cons: "The online reservation had me pick seats for my family, those seats were emailed to me, then when I checked in and got our boarding passes, the seats had changed! Wouldn't have been a big deal, but I had already memorized our seats, so I looked like a moron when I insisted seats that were not ours anymore were ours!"
Pros: "Food available was good."
Cons: "Very tight space- could not reach floor when person in front of me moved seat into recline position. Could not get out of seat to go to bathroom when my seat mates were sleeping. Tough to load- tight spaces."
Cons: "2.5 hour delay on the ground - very poor communication from Crew"
Pros: "The flight was crowded, but what can you expect? Turbulence prevented beverage service. The flight arrived early but had to wait to land."
Cons: "inflight entertainment wasn't working on my seat only which made my 6 hour flight seem even longer :("
Pros: "Wi-Fi was great. Watched two movies. Flight was on time and painless"
Cons: "Only complimentary snack was pretzels and only a cup of water."
Pros: "Despite getting no updates, our flight itinerary was changed from a 3.30pm flight to a 9.20pm flight. Unfortunately this was after landing from Milan at 1.30 with two small children so we had already had a very long day. We absolutely never would have booked this flight itinerary had we known of the change."
Cons: "I am beyond stunned that our flight itinerary was changed from 3.30pm to 9.20pm with no notification. This is absolutely unreasonable and inexcusable made even worse that we had already had a very long journey from Milan to JFK with two small children. Evidently the issue was that we booked via a 3rd party off the kayak site and not directly with British airways. When American airways changed the flight from 3.30 to 3.25, the 3rd party company failed to file for our updated itinerary so British air/American air bumped us to the next flight at 9.20pm. We have long been loyal to kayak feeling it provides the best breadth of options and good pricing. Now we may use kayak to see all the options but I can’t booking directly with kayak anymore after this complete disaster. We ended up renting a car and driving from jfk to Boston, getting home 23 hours after our journey had started, stressed, beyond exhausted and now have to return the rental car. Thanks kayak."
Cons: "Had to drive 100 miles to catch second leg of trip."
Cons: "We flew from Rome to JFK and arrived at 12:40 pm only to find out that our 3:30 pm flight had been cancelled a long time ago. No one had notified us of our new booking on a 9:10 flight to Boston. No one at American or British Airways could provide us with an earlier departure or compensate us to take alternative transportation. Our 9:10 flight was then delayed until 10:50 pm. We arrived in Boston at 12:02 am, 11 1/2 hours after our arrival at JFK from Rome. This was not a very friendly welcome home. We never would have booked such an extended delay as we only live 4 hours from New York City."
Cons: "the payment didn't work but I got no notification. When I got to the airport I couldn't check in. It took a lot of time with more fee to figured it out. A terrible experience"
Pros: "One was great and one was not helpful and was condescending"
Pros: "Staff was polite and friendly. It was a great experience!"
Pros: "Great, friendly crew and excellent customer service from flight attendants."
Pros: "Seats were pretty comfortable"
Cons: "In-flight entertainment depended on the Wi-Fi working. It did not work the whole flight."
Pros: "The plane was nice and in good shape. They had beverage service for a very quick flight which is nice. Can't rate food or entertainment because only hour or so flight."
Cons: "It was freezing in the plane and I'm never cold. When I asked for a blanket they had none!!! They had just announced whatever they can do to make your flight more comfortable ask them. Not true, just words. Disappointed after the great treatment after flying ANA."
Pros: "Friendly crew, efficient boarding, easy flight"
Cons: "Nothing on tv unless you pay for it. Like, nothing."
Pros: "That seats next to me were empty so I was able to sleep comfortably."
Cons: "That my ears don't work well, so it's hard to hear the movies."
Cons: "Because of missed connection I had to go from Dulles to Reagan airport"
Pros: "I got home safe."
Cons: "The customer service was mediocre. The selection of complementary beverage was minimal compared to other airlines. The staff are disgruntled and sometimes rude. There was always some sort of mechanical problems with the plane going to Puerto Plata and coming back. On the way to DR we had to divert to Miami because of problems with Navigation. They made us wait seven hours and gave us a voucher for food at the last minute. People had already bought food. I would not recommend United to none of my associates."
Pros: "The flight was as comfortable as can be. I really appreciated the great cup of coffee brewed. This was the 2nd and final segment of an overnight itinerary. What else can be said?"
Pros: "Free TV since we were 2 hours delayed"
Cons: "4 delays in 1 day on 2 flights. 2 gate changes with no relay of info and to top it all off my wife and i were reassigned to separate seats at the last minute by the airline and very rudely told to deal with it and to calm down when I simply asked why. We were appalled and embarrassed in front of many others in the gate boarding area. The gate agent in Houston has no place in customer service and was on some kind of a power trip. This surprised me with recent events. We are done with United now for many reasons"
Cons: "The fact that I have to pay extra for food or any form of entertainment is appalling compared to other airlines. $20 for WIFI? That's a joke."
Cons: "I booked one of the big seats in front. It was great."
Cons: "Terrible as always. Lost my carryon, which I had to pay to check. Checked in an hour before the flight departed. No reason why the bag didn't make the flight. Seats don't recline. Make you pay for a soft drink."
Pros: "It got us back home"
Cons: "Not as cheap as you think after all the add ons"
Pros: "new planes, competent employees"
Cons: "seats too close, don't lean back-- can't sleep."
Pros: "We got here early and it was a very very smooth flight."
Pros: "Everything went fine. We knew how to avoid additional fees."
Cons: "Seats were close and don't recline."
Pros: "Liked the way Spirit Airlines were transparent in letting us know all the additional charges at the time of booking itself."
Cons: "entertainment system can be added to the flights , as we don't get coffe or Tea for free , we can be occupied by watching some channel."
Pros: "The flight was on time and boarding was effficient."
Cons: "Seats are not comfortable (plastic, no reclining possible), they charge $3.00 for water! They add for carry-on. Staff is loud and makes announcements for selling Spirit products over the loudspeaker. Impossible to sleep. My worst flight ever in terms of comfort."
Pros: "Everyone was so friendly and helpful"
Cons: "That I couldn't take all the friendly and helpful people home with me...to make them a proper meal"
Pros: "And then had to wait at the gate while another plane left."
Book cheap flights from Caribbean to Boston
Recent round-trip flight deals
10/21Sat
nonstopSpirit Airlines
4h 10mSJU-BOS
10/28Sat
nonstopSpirit Airlines
4h 08mBOS-SJU
$91
10/14Sat
nonstopSpirit Airlines
4h 10mSJU-BOS
10/18Wed
nonstopSpirit Airlines
4h 08mBOS-SJU
$92
10/17Tue
nonstopSpirit Airlines
4h 10mSJU-BOS
10/25Wed
nonstopSpirit Airlines
4h 08mBOS-SJU
$93
10/17Tue
nonstopSpirit Airlines
4h 10mSJU-BOS
10/25Wed
nonstopSpirit Airlines
4h 08mBOS-SJU
$94
10/18Wed
nonstopSpirit Airlines
4h 10mSJU-BOS
10/25Wed
nonstopSpirit Airlines
4h 08mBOS-SJU
$101
10/21Sat
nonstopSpirit Airlines
4h 10mSJU-BOS
10/28Sat
nonstopSpirit Airlines
4h 08mBOS-SJU
$102
10/17Tue
nonstopSpirit Airlines
4h 10mSJU-BOS
10/25Wed
nonstopSpirit Airlines
4h 08mBOS-SJU
$103
10/17Tue
1 stopSpirit Airlines
16h 58mSJU-BOS
10/25Wed
nonstopSpirit Airlines
4h 08mBOS-SJU
$105
10/14Sat
1 stopMultiple Airlines
28h 59mSJU-BOS
10/25Wed
1 stopMultiple Airlines
13h 28mBOS-SJU
$152
10/19Thu
1 stopMultiple Airlines
21h 34mSJU-BOS
10/25Wed
1 stopMultiple Airlines
22h 17mBOS-SJU
$157
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Recent one-way flight deals
10/25Wed
1 stopSpirit Airlines
16h 58mSJU-BOS
$59
10/27Fri
1 stopFrontier
8h 40mSJU-BOS
$62
10/20Fri
nonstopSpirit Airlines
4h 10mSJU-BOS
$63
11/2Thu
1 stopSpirit Airlines
6h 48mSJU-BOS
$64
10/20Fri
nonstopSpirit Airlines
4h 10mSJU-BOS
$65
10/2Mon
1 stopSpirit Airlines
11h 20mSJU-BOS
$66
11/2Thu
nonstopSpirit Airlines
4h 10mSJU-BOS
$67
10/24Tue
1 stopFrontier
13h 28mBQN-BOS
$93
12/10Sun
nonstopJetBlue
4h 16mSJU-BOS
$129
1/10Wed
1 stopJetBlue
8h 27mBQN-BOS
$132
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Last minute flights from Caribbean to Boston
Last minute flight, train and bus deals
9/24Sun
multi-stopSpirit Airlines
18h 09mSJU-BOS
10/3Tue
multi-stopSpirit Airlines
22h 28mBOS-SJU
$218
9/25Mon
multi-stopSpirit Airlines
14h 52mSJU-BOS
10/3Tue
multi-stopSpirit Airlines
22h 28mBOS-SJU
$219
9/23Sat
nonstopDelta
4h 21mSJU-BOS
10/27Fri
nonstopDelta
4h 15mBOS-SJU
$350
9/26Tue
nonstopJetBlue
3h 59mSTI-BOS
11/4Sat
nonstopJetBlue
3h 43mBOS-STI
$394
9/23Sat
nonstopJetBlue
4h 05mSDQ-BOS
10/3Tue
nonstopJetBlue
4h 08mBOS-SDQ
$400
9/23Sat
multi-stopUnited Airlines
7h 54mSTI-BOS
10/1Sun
multi-stopUnited Airlines
14h 26mBOS-STI
$401
9/25Mon
multi-stopUnited Airlines
17h 05mSTI-BOS
11/4Sat
multi-stopUnited Airlines
7h 14mBOS-STI
$402
9/26Tue
multi-stopAmerican Airlines
14h 09mSDQ-BOS
10/3Tue
multi-stopAmerican Airlines
9h 10mBOS-SDQ
$420
9/25Mon
multi-stopAmerican Airlines
22h 15mSTI-BOS
10/10Tue
multi-stopAmerican Airlines
6h 56mBOS-STI
$424
9/23Sat
nonstopDelta
4h 21mSJU-BOS
9/26Tue
nonstopDelta
4h 19mBOS-SJU
$452