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Find cheap flights from Caribbean to Massachusetts from $53

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Caribbean to Massachusetts departing on 6/1. 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
0 bags
Sun 6/9
Sun 6/16

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Good to know

Low season

January

High season

July

Cheapest flight

$53
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from San Juan Airport to Boston

FAQs for booking flights from Caribbean to Massachusetts

  • How does KAYAK find such low prices on flights from Caribbean to Massachusetts?

    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 Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts 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 Massachusetts?

    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 Massachusetts 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 Massachusetts?

    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 Massachusetts from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Caribbean to Massachusetts

 
Need help choosing which airline to fly with from Caribbean to Massachusetts? 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
Caribbean AirlinesOverall score based on 186 reviews
7.6Comfort
8.3Crew
6.7Food
8.2Boarding
6.7Entertainment
Airline reviews

There was no music on the flights unless you came with your headset.

10.0 Excellentsusan, Apr 2024MIA - POS
Read more about Caribbean Airlines reviews

There was no music on the flights unless you came with your headset.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

It was good but the food was small for the duration of the flight.

I wrote to the entertainment and food OK because it was non-applicable All excellent

Checking in online still requires going on the physical check in line

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

The captain was great he made jokes and make thebflight very comfortable. Alerted us about the islands we flew over and Yolandra and her team took great care of us, very personable.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

Non operational toilet, non operational charging outlets and my air didn’t work.

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Easy boarding and deplaning. Short flight. Water was given but that was it.

Flight was delayed a bit since booking but otherwise everything was very good.

While this is a VERY SMALL plane; take-off to landing was fine. It's the constant departure time changes that wore me out and I'll try to never use this inconsistent airway again. Four delays in one day. Done!!!!!!

This has been, by far, my worst experience with an airline company. I had a reservation for a Tuesday at 8:30 pm departure from Gainesville, FL (1.5 hours - direct flight) I received an email on Monday that my flight had been changed to Monday at night to depart from Jacksonville, FL (and it was an 11 .5 hours flight ). There was no way I would have had the time to gather my things, drive 1.5 hours to the Jacksonville airport, and make it on time to board the plane. Besides, I had a full day of work on Tuesday. The only good thing I xan say about Silver airlines is that they did give me a refund, but I had to wait about 4 hours for a call back

Book cheap flights from Caribbean to Massachusetts

Recent round-trip flight deals

6/4Tue
nonstopFrontier
4h 21mSJU-BOS
6/11Tue
nonstopFrontier
4h 00mBOS-SJU
$90
5/22Wed
1 stopSpirit Airlines
9h 37mSJU-BOS
5/22Wed
1 stopSpirit Airlines
6h 42mBOS-SJU
$97
6/7Fri
nonstopJetBlue
4h 08mSJU-BOS
6/14Fri
nonstopJetBlue
4h 05mBOS-SJU
$248
6/12Wed
nonstopJetBlue
4h 14mSJU-BOS
6/14Fri
nonstopJetBlue
4h 05mBOS-SJU
$253
5/24Fri
1 stopAmerican Airlines
8h 50mMBJ-BOS
8/24Sat
1 stopAmerican Airlines
9h 55mBOS-MBJ
$316
7/4Thu
1 stopAmerican Airlines
18h 57mMBJ-BOS
8/24Sat
1 stopAmerican Airlines
9h 55mBOS-MBJ
$326
6/11Tue
1 stopCopa Airlines
10h 14mPOS-BOS
9/10Tue
1 stopCopa Airlines
10h 07mBOS-POS
$396
6/11Tue
1 stopCopa Airlines
10h 14mPOS-BOS
8/20Tue
1 stopCopa Airlines
10h 09mBOS-POS
$431
6/12Wed
2 stopsAir Canada
24h 28mMBJ-BOS
10/21Mon
1 stopAir Canada
20h 55mBOS-MBJ
$488
5/29Wed
1 stopAir Canada
24h 58mMBJ-BOS
10/20Sun
1 stopAir Canada
26h 40mBOS-MBJ
$513

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Recent one-way flight deals

6/1Sat
nonstopSpirit Airlines
4h 24mSJU-BOS
$53
6/5Wed
nonstopSpirit Airlines
4h 14mSJU-BOS
$54
6/20Thu
nonstopFrontier
4h 08mSJU-BOS
$69
6/20Thu
nonstopFrontier
4h 08mSJU-BOS
$71
7/1Mon
nonstopJetBlue
4h 00mSJU-BOS
$142
6/13Thu
1 stopJetBlue
7h 33mSTT-BOS
$153
5/24Fri
1 stopAmerican Airlines
6h 53mSJU-BOS
$166
5/24Fri
1 stopAmerican Airlines
6h 53mSJU-BOS
$170
6/12Wed
1 stopCopa Airlines
10h 14mPOS-BOS
$222
6/18Tue
1 stopCopa Airlines
13h 15mPUJ-BOS
$226

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Last minute flights from Caribbean to Massachusetts

Last minute flight, train and bus deals

5/11Sat
nonstopSpirit Airlines
4h 24mSJU-BOS
5/18Sat
nonstopSpirit Airlines
4h 06mBOS-SJU
$174
5/11Sat
nonstopSpirit Airlines
4h 24mSJU-BOS
5/17Fri
nonstopSpirit Airlines
4h 06mBOS-SJU
$213
5/11Sat
nonstopSpirit Airlines
4h 24mSJU-BOS
5/21Tue
multi-stopSpirit Airlines
9h 35mBOS-SJU
$220
5/11Sat
multi-stopFrontier
11h 57mSJU-BOS
5/18Sat
multi-stopFrontier
14h 40mBOS-SJU
$244
5/11Sat
multi-stopAmerican Airlines
8h 42mSJU-BOS
5/18Sat
multi-stopAmerican Airlines
13h 27mBOS-SJU
$349
5/12Sun
multi-stopAmerican Airlines
15h 23mSJU-BOS
5/19Sun
multi-stopAmerican Airlines
11h 35mBOS-SJU
$356
5/12Sun
multi-stopFrontier
19h 32mSDQ-BOS
6/1Sat
multi-stopFrontier
25h 51mBOS-SDQ
$370
5/10Fri
nonstopJetBlue
4h 14mSJU-BOS
5/13Mon
nonstopJetBlue
3h 59mBOS-SJU
$396
5/14Tue
multi-stopJetBlue
13h 50mSDQ-BOS
5/19Sun
nonstopJetBlue
4h 06mBOS-SDQ
$397
5/10Fri
multi-stopCopa Airlines
28h 58mBGI-BOS
5/28Tue
multi-stopCopa Airlines
22h 01mBOS-BGI
$556

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