$75 Find Cheap Flights from Caribbean Islands to Massachusetts

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Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$75
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from San Juan Airport to Boston

FAQs for booking flights from Caribbean Islands to Massachusetts

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean Islands to Massachusetts 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 Islands 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 from Caribbean Islands to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 from Caribbean Islands to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Massachusetts?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $260.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Friday where round-trip tickets can be as cheap as $214. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $282 on average.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the morning, when round-trip flights cost $218 on average. Morning departures are around 23% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $282.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Caribbean Islands found in the last 72 hours was to Boston, at $114 round-trip. The most popular route is Oranjestad (AUA) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $114.

  • What is the cheapest month to fly from Caribbean Islands to Massachusetts?

    The cheapest month for flights from Caribbean Islands to Massachusetts is February, when tickets cost $445 (return) on average. On the other hand, the most expensive months are August and January, when the average cost of round-trip tickets is $557 and $551 respectively.

  • How far in advance should I book a flight from Caribbean Islands to Massachusetts?

    To get a below average price on the flight from Caribbean Islands to Massachusetts, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Caribbean Islands to Massachusetts takes 11h 24m, covering a distance of 1730 miles. The shortest route is Nassau (NAS) to Boston (BOS) with an average flight time of 3h 26m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (77% of total searches to Massachusetts). The next most popular destinations are Hartford (21%) and Albany (1%). Searches for flights to Worcester (1%), to New Bedford (0%) and to Provincetown (0%) are also popular.

Top 5 airlines serving from Caribbean Islands to Massachusetts

 
Need help choosing which airline to fly with from Caribbean Islands 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.
8.0
DeltaOverall score based on 7950 reviews
8.2Boarding
7.9Comfort
7.3Food
7.9Entertainment
8.5Crew
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Boarding was tough as we had to take a bus out to the plane and walk up a lot of stairs. Difficult with heavy carry-ons that said I got an entire empty row of seats, which was excellent for an international flight. Food was very mediocre but happy with the comfort so not complaining.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

Delta is better for short flights and very low need for customer service. Avoid for longer flights

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

The gate and ground staff were excellent, friendly, went out of their way to acknowledge my Mosaic status. The plane was an older Airbus, so the seats were a little worn. The in flight attendant was not very nice, and seemed to be annoyed to be at work or be on this flight. Flight was fast and we landed early and pilots kept us informed.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

The inflight system with their wifi is a hot mess and doesn't work. Separately they do, but when you try to do theoretically simple things like pair a device for control it all falls apart

It was too hot in the cabin. The AC did not help.

The regular feedback of any changes to our flights. The Jetblue staff were very helpful. Our flights were great. Lots of leg room!

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

The pilots are always hauling in the sky. No issues with boarding only problem was layover was shortened too much by weather but luckily the next flight was still boarding and did not missit

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Departure was right on time. The Orlando base crew from Atlanta to Puerto Rico was the BEST. The return flight crew was OK.

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

Book cheap flights from Caribbean Islands to Massachusetts

Recent round-trip flight deals

7/3Thu
nonstopSpirit Airlines
4h 07mSJU-BOS
7/6Sun
nonstopSpirit Airlines
3h 54mBOS-SJU
$147
7/3Thu
nonstopSpirit Airlines
4h 07mSJU-BOS
7/8Tue
1 stopSpirit Airlines
13h 04mBOS-SJU
$148
9/25Thu
nonstopDelta
4h 12mSJU-BOS
11/2Sun
nonstopDelta
4h 12mBOS-SJU
$218
6/26Thu
nonstopJetBlue
4h 07mSJU-BOS
7/12Sat
nonstopJetBlue
4h 05mBOS-SJU
$226
11/1Sat
1 stopUnited Airlines
8h 09mSJU-BOS
11/9Sun
2 stopsUnited Airlines
10h 57mBOS-SJU
$227
6/26Thu
nonstopJetBlue
4h 07mSJU-BOS
7/12Sat
nonstopJetBlue
4h 04mBOS-SJU
$231
10/1Wed
2 stopsAmerican Airlines
17h 39mSJU-ALB
10/7Tue
2 stopsAmerican Airlines
10h 52mALB-SJU
$251
7/3Thu
nonstopDelta
4h 11mSJU-BOS
7/7Mon
nonstopDelta
4h 06mBOS-SJU
$263
9/30Tue
2 stopsUnited Airlines
13h 12mSJU-ALB
10/7Tue
2 stopsUnited Airlines
14h 38mALB-SJU
$271
10/3Fri
2 stopsAmerican Airlines
10h 49mSJU-BOS
10/7Tue
2 stopsAmerican Airlines
9h 00mBOS-SJU
$280

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Recent one-way flight deals

6/26Thu
nonstopSpirit Airlines
4h 07mSJU-BOS
$75
7/13Sun
nonstopSpirit Airlines
4h 17mSJU-BOS
$76
6/25Wed
nonstopJetBlue
4h 05mSJU-BOS
$109
6/25Wed
1 stopUnited Airlines
7h 06mSJU-BOS
$114
11/4Tue
nonstopJetBlue
4h 11mSJU-BOS
$129
6/24Tue
2 stopsAmerican Airlines
10h 24mSJU-BOS
$134
7/8Tue
2 stopsUnited Airlines
13h 59mSJU-ALB
$143
7/1Tue
2 stopsAmerican Airlines
15h 44mSJU-BOS
$145
11/6Thu
1 stopDelta
8h 31mSJU-BDL
$153
7/25Fri
nonstopDelta
4h 14mSJU-BOS
$167

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Last minute flights from Caribbean Islands to Massachusetts

Last minute flight, train and bus deals

6/14Sat
multi-stopFrontier
7h 07mSJU-BOS
6/16Mon
multi-stopFrontier
9h 50mBOS-SJU
$221
6/14Sat
multi-stopFrontier
7h 07mSJU-BOS
6/19Thu
multi-stopFrontier
11h 49mBOS-SJU
$227
6/14Sat
multi-stopSpirit Airlines
12h 50mSJU-BDL
6/21Sat
multi-stopSpirit Airlines
9h 23mBDL-SJU
$284
6/15Sun
nonstopSpirit Airlines
4h 07mSJU-BOS
6/17Tue
multi-stopSpirit Airlines
7h 55mBOS-SJU
$305
6/16Mon
nonstopJetBlue
4h 15mMBJ-BOS
9/2Tue
nonstopJetBlue
4h 28mBOS-MBJ
$359
6/17Tue
multi-stopJetBlue
6h 28mSJU-BOS
6/23Mon
nonstopJetBlue
4h 04mBOS-SJU
$373
6/17Tue
multi-stopAmerican Airlines
10h 36mSJU-BDL
6/25Wed
multi-stopAmerican Airlines
10h 10mBDL-SJU
$386
6/17Tue
multi-stopAmerican Airlines
10h 51mSJU-BOS
6/22Sun
multi-stopAmerican Airlines
17h 06mBOS-SJU
$388
6/13Fri
nonstopDelta
4h 11mSJU-BOS
6/15Sun
nonstopDelta
4h 08mBOS-SJU
$454
6/13Fri
multi-stopDelta
9h 09mSJU-BOS
6/15Sun
nonstopDelta
4h 08mBOS-SJU
$459

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Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Caribbean Islands

Cabin classes available on flights to Caribbean Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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