$67 Find Cheap Flights from Caribbean to Massachusetts

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Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$67
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 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 from Caribbean 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 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 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 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 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 $263.

  • 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 $215. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $284 on average.

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

    The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $219 on average. Morning departures are around 20% 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 $280.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Caribbean found in the last 72 hours was to Boston, at $140 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 $140.

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

    The cheapest month for flights from Caribbean to Massachusetts is February, when tickets cost $449 (return) on average. On the other hand, the most expensive months are August and July, when the average cost of round-trip tickets is $569 and $557 respectively.

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

    To get a below average price on the flight from Caribbean 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 to Massachusetts takes 10h 04m, covering a distance of 1759 miles. The shortest route is San Juan Luis Munoz Marin Intl Airport (SJU) to Hartford (BDL) with an average flight time of 3h 53m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (74% of total searches to Massachusetts). The next most popular destinations are Hartford (23%) and Albany (2%). Searches for flights to Worcester (1%), to Provincetown (0%) and to New Bedford (0%) are also popular.

Reviews of the top 5 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.
8.0
DeltaOverall score based on 7956 reviews
8.2Boarding
7.9Entertainment
8.5Crew
7.9Comfort
7.3Food
Airline reviews

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

4.0 OkayAnonymous, Jul 2025ATL - ROC
Read more Delta reviews

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Our flight was canceled after several delays. No hotel vouchers offered, minimal help for resolution leave me ultimately to cancel and book on an other airline. Then waited to get bags for more than 3 hours This whole experience has been awful!!!

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

flight cancelled after 2 delays. left us sitting in JFK at 1am. no customer service to assist rebooking.

To not have food or proper snacks on a 5 hour flight was the worst.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

Ground crew gave me interference about carrying a laptop and a small shoulder bag, even though I told them I traveled with them all the time. I then placed my laptop bag in my carryon and took out a medical device, and ground crew still tried to give interference. I had to remind them that medical devices don't count towards luggage limits. It was quite annoying and unne

Overall fine, but the delay was annoying and the reasons for the delay were not communicated. The crew on board were phenomenal!

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

Although our flight had delays due to three different reasons, it was good. Staff continued to update us which made every one comfortable. We felt the captain and crew had our safety in mind the entire time and no one seemed to lose their patience.

I've flown Spirit many times. However, they seem to be getting worse. I don't understand how the contracts with the gates at the airport works, but Spirit never seems to have a gate ready when we land. This happened again on this flight. And once again, baggage took forever to arrive at the baggage claim belt. This time it was about 45 minutes to an hour, late at night, when the airport was not crowded. On a previous trip, they lost the luggage cart and we were all waiting for about 3 hours for our luggage. Plus, I did get a deal through Kayak on a flight that was shown sold out on Spirit's site. However, by the time I added all the luggage, and didn't even pick seats, I could have taken any direct flight I wanted through Delta. I'm about done with Spirit.

I enjoyed my flight, it was pretty smooth and we landed earlier than eta.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

It was okay delay was long but I made it

Flight was cancelled. No reason given. No apologies. Next available flight is two days later. Ruined our 4th of July plans.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

Flight delayed over 3 or 4 hours because no captain to fly plane. I couldn’t make a connection and had to wait 9 hours for another flight. Had to fly red eye flight. Sucks

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

Book cheap flights from Caribbean to Massachusetts

Recent round-trip flight deals

7/24Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
7/27Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
$144
8/29Fri
nonstopFrontier
4h 00mSJU-BDL
9/1Mon
nonstopFrontier
3h 55mBDL-SJU
$162
9/6Sat
1 stopDelta
9h 19mSJU-ALB
9/17Wed
1 stopDelta
9h 40mALB-SJU
$233
10/22Wed
1 stopAmerican Airlines
7h 30mSJU-BDL
10/31Fri
1 stopAmerican Airlines
7h 39mBDL-SJU
$236
10/7Tue
2 stopsAmerican Airlines
11h 02mSJU-BDL
10/14Tue
2 stopsAmerican Airlines
13h 25mBDL-SJU
$240
8/15Fri
nonstopJetBlue
4h 07mSJU-BOS
8/17Sun
nonstopJetBlue
4h 04mBOS-SJU
$244
8/7Thu
nonstopDelta
4h 14mSJU-BOS
8/12Tue
nonstopDelta
4h 06mBOS-SJU
$245
7/25Fri
nonstopJetBlue
4h 07mSJU-BOS
7/28Mon
nonstopJetBlue
4h 06mBOS-SJU
$246
8/15Fri
1 stopUnited Airlines
28h 38mMBJ-BOS
9/18Thu
2 stopsUnited Airlines
42h 03mBOS-MBJ
$321
9/6Sat
2 stopsUnited Airlines
20h 07mPUJ-BOS
9/13Sat
2 stopsUnited Airlines
9h 55mBOS-PUJ
$352

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Recent one-way flight deals

7/24Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
$67
7/24Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
$71
7/31Thu
nonstopFrontier
4h 00mSJU-BDL
$104
10/24Fri
1 stopDelta
8h 53mSJU-ALB
$108
8/28Thu
nonstopFrontier
4h 00mSJU-BDL
$108
9/13Sat
1 stopDelta
10h 13mSJU-BDL
$118
9/20Sat
2 stopsAmerican Airlines
18h 08mSJU-BDL
$120
8/2Sat
nonstopJetBlue
4h 10mSJU-BOS
$122
7/25Fri
nonstopJetBlue
4h 05mSJU-BOS
$123
7/19Sat
1 stopAmerican Airlines
10h 03mSJU-BOS
$133

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Last minute flights from Caribbean to Massachusetts

Last minute flight, train and bus deals

7/17Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
8/10Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
$184
7/17Thu
nonstopSpirit Airlines
4h 17mSJU-BOS
7/20Sun
nonstopSpirit Airlines
4h 05mBOS-SJU
$186
7/17Thu
nonstopJetBlue
4h 07mSJU-BOS
8/13Wed
nonstopJetBlue
4h 04mBOS-SJU
$250
7/18Fri
nonstopJetBlue
4h 05mSJU-BOS
7/26Sat
nonstopJetBlue
4h 04mBOS-SJU
$251
7/17Thu
nonstopFrontier
4h 00mSJU-BDL
7/28Mon
nonstopFrontier
3h 55mBDL-SJU
$256
7/19Sat
nonstopFrontier
4h 00mSJU-BDL
7/21Mon
multi-stopFrontier
29h 56mBDL-SJU
$258
7/16Wed
multi-stopAmerican Airlines
10h 50mSJU-BOS
7/22Tue
multi-stopAmerican Airlines
8h 59mBOS-SJU
$260
7/17Thu
nonstopDelta
4h 14mSJU-BOS
7/21Mon
nonstopDelta
4h 06mBOS-SJU
$264
7/16Wed
multi-stopAmerican Airlines
10h 50mSJU-BOS
7/19Sat
multi-stopAmerican Airlines
16h 45mBOS-SJU
$265
7/15Tue
nonstopDelta
4h 14mSJU-BOS
8/26Tue
nonstopDelta
4h 06mBOS-SJU
$278

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Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Caribbean

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

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