$129 Find Cheap Flights from Caribbean to Massachusetts

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1 adult, Economy, 0 bags

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Good to know

Low seasonJanuary
Cheapest flight$129
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from San Juan Airport to Hartford

Flights from Caribbean to Massachusetts: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Caribbean to Massachusetts 
JasmaryFlew with Spirit Airlines
SJU
-
BOS
Feb 2026
I would advice passengers to bring their own snack as most items are out of stock
slovely08Flew with JetBlue
AUA
-
BOS
Dec 2024
Be prepared for long security times, you have to clear customs in Aruba, and there can be a substantial line if you get there at the wrong time. They tell you to be there 3 hours early for a reason.

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 airlines fly most frequently to Massachusetts?

    Caribbean and Massachusetts are connected by different airlines. The airlines that fly that route the most regularly are JetBlue (113 flights per week), Aer Lingus (28 flights per week), and Icelandair (21 flights per week).

  • How many airports are there in Massachusetts?

    There are 8 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 94% of all flights arriving there.

  • 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 $293.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Thursday where round-trip tickets can be as cheap as $281. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $374 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 evening, when round-trip flights cost $256 on average. Morning departures are around 15% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $352.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Caribbean found in the last 7 days was to Boston, at $192 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 7 days was $192.

  • 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 $368 (return) on average. On the other hand, the most expensive months are August and May, when the average cost of round-trip tickets is $637 and $607 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 2 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

  • How many cities have direct flights to Massachusetts?

    From Caribbean, there are direct flights to Massachusetts from 11 cities. The city with the most direct flights is San Juan, with 146 direct flights each week.

  • How many direct flights to Massachusetts are there each day?

    There are around 34 direct flights from within Caribbean to Massachusetts every day. Most flights (63%) depart in the afternoon.

  • How many direct flights to Massachusetts are there each week?

    Each week there are around 233 direct flights from within Caribbean to Massachusetts. The most common day for departures is Saturday, with 18% of flights taking off on this day.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Caribbean to Massachusetts takes 10h 20m, covering a distance of 1745 miles. The shortest route is Providenciales (PLS) to Boston (BOS) with an average flight time of 3h 45m.

  • How many long-haul flights are there to Massachusetts each week?

    Each week, there are 205 medium-haul flights (3-6 hour flight duration) and 28 short-haul flights (up to 3 hour flight duration) to Massachusetts. There aren't any long-haul flights (6-12 hour flight duration).

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (67% of total searches to Massachusetts). The next most popular destinations are Hartford (31%) and Albany (2%). Searches for flights to Worcester (0%), to New Bedford (0%) and to Provincetown (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.
7.9
DeltaOverall score based on 8423 reviews
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
7.8Comfort
Airline reviews

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

6.0 GoodAnonymous, May 2026
GNV - ATL
Read more Delta reviews

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Flight was delayed. Then eventually cancelled. The female staff that was announcing overhead was unprofessional. She was telling everyone that the company is not going to give any money for taxi, hotel etc. then eventually the flight was cancelled.

My service light was on 15 minutes before I had to get up and find a glass of ice. And I was in business class. The meals were not for either my wife and I. She did not eat the entire 10 hour flight and I managed a bowl of soup. I was expecting much more from business with what we paid.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

Much better than I expected. I had an economy ticket so I was really happy the flight was so comfy and the service so generous. Passengers were all polite too.

Jet blue is always good - the one weird thing was that they started boarding about 20-30 minutes before the official boarding time on the app. Just something to be aware of!

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

My flight today was cancelled because it was Spirit Airlines but have received no refund.

THEY WENT OUT OF BUSINESS AND CANCELED FLIGHT. REPLACEMENT FLIGHTS WERE 300% HIGHER SO MY FAMILY COULD NOT GET TOGETHER. WHY AM I GETTING THIS SURVEY?????

If there WAS a flight it would have been EXCELENT..Maybe?

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

There was no flight. Spirit went bankrupt Right before my departure and kayak did not refund me any money. I would like my refund kayak. How can I get it? Please let me know. Thank you

Flights were canceled due to airline shutting down and haven’t received a reimbursement. Had to book last minute new flights which were expensive

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Had a flight change had to get a credit.will I get my money back.

Shut down without prior notice End up with spending lots of extra $$$

There was a crack in my window seal. And Spirit is now closed forever.

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.