$101 Find Cheap Flights from Caribbean to Massachusetts

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 6/18. 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
1 adult, Economy, 0 bags

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Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 8% 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 (142 flights per week), Aer Lingus (34 flights per week), and Icelandair (24 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 91% 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 $301.

  • 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 $306. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $463 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 $278 on average. Morning departures are around 6% cheaper 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 $362.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Caribbean found in the last 5 days was to Boston, at $162 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 5 days was $162.

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

    The cheapest month for flights from Caribbean to Massachusetts is December, when tickets cost $209 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $324 and $310 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 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

  • How many cities have direct flights to Massachusetts?

    From Caribbean, there are direct flights to Massachusetts from 12 cities. The city with the most direct flights is San Juan, with 158 direct flights each week.

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

    There are around 39 direct flights from within Caribbean to Massachusetts every day. Most flights (48%) depart in the afternoon.

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

    Each week there are around 270 direct flights from within Caribbean to Massachusetts. The most common day for departures is Monday, with 17% of flights taking off on this day.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Caribbean to Massachusetts takes 11h 20m, covering a distance of 1733 miles. The shortest route is Nassau (NAS) to Boston (BOS) with an average flight time of 3h 24m.

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

    Each week, there are 240 medium-haul flights (3-6 hour flight duration) and 30 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 (72% of total searches to Massachusetts). The next most popular destinations are Hartford (25%) and Albany (2%). Searches for flights to Worcester (0%), to New Bedford (0%) and to West Tisbury (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 8399 reviews
8.5Crew
8.1Boarding
7.2Food
7.8Comfort
7.8Entertainment
Airline reviews

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

4.0 OkayMichelle, Jun 2026
ATL - PIT
Read more Delta reviews

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

The seats were really comfortable. Flight crew were friendly with passengers. Overall was a great flight.

Arrived early, comfortable seats (Comfort+). Mediocre food, poor wifi (intermittent).

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Great crew, flight on time, luggage pick up a breeze

Was on time, normal boarding. The worst flight attendents and service I ever seen,, can't believe Delta can have such service. Bathroom was dirty and no toilet paper, paper towels and used toilet paper all over the floor, when I tried to tell flight attendant she didn't even let me to finish and turn around. Very rude. Wi fi didn't work.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Referencing ANA'S service to Japan and the return on UA, the pillow was awful, the crew was not very attentive, and the food was bizarre and tasted okay. Whoever's idea it was to make vegetable tempera in a steam capsule should probably revisit that. Since it was the vegetarian option, it was my only choice.

Crew was great! Good meals. Had room to stretch out

Our flight was delayed 2.5 hours from Lisbon to DC so we missed our connection to Seattle that would have arrived at about 9 PM. The agent initially said we had to stay overnight in DC and there were no other options to put us on to get us to Seattle. While on board I discovered a flight via American he could have put us in but by the time we arrived in DC that was sold out. We were then put on a flight to San Francisco that was also delayed then arrived in San Francisco and our flight to Seattle was also delayed so we ended up not arriving until 2:15 am. Our son could not pick us up so we ended up having to pay over $100 to Uber home. This is the second trip with United that the flight has been delayed causing us to miss an evening in Las Vegas and we were given nothing.

Boarding was smooth and efficient. The only food was some pretzels, but it was a short flight. Not much to order if you were hungry.

Crew were welcoming, accommodating and they worked hard to find places for all carry on.

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Destroyed my suitcase. Tired of talking about it. Cancelling my unite mileage plus account.

Read the fine print. This was my flight home. I booked my flight for the quickest way home. Had a carry-on and a personal item. Same as my outbound flight. Apparently I needed to pre-pay extra for my carry-on. When I checked in, I was told that I had to check it. I said I’ll pay for it, and was told that this wasn’t an option anymore. They said I still had to pay $50 to check my carry-on. I told them I’ll pay whatever to just carry it in as intended. I was not allowed, so eventually I paid $50 to check my carry-on under a plane that was half full, with overhead compartments that were even less full. My white carry-on suitcase was practically destroyed getting from Idaho falls to Denver to Orange County. The low price air fair was a bait and switch. Got me to the gate, made me pay extra, then didn’t even allow me to pay for a carry on. Not to mention that I paid the $8 for WiFi that didn’t work. All to get my suitcase destroyed. I don’t think I’m going to even keep my Untied mileage plus membership and card. Apparently, membership does not have its privileges for this one.

The flight was delayed, they didn’t even have water for the toilets or for drinks

Even through the flight was delayed due to storms near IAH The flight was great! The crew was so hospitable and professional

The middles seats on the 777 airplane are very small. I am only five feet tall and my knees were touching the seat in front of me and the is no leg room if you have a person item under the seat. The food was horrible, spicy sauces, tasteless bread, and wilted/brown lettuce. Keep it simple. The staff was mediocre., one minute loud and chastising, and the other friendly. We liked how clear and easy to understand the entry process in to the US was.

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

It wa sort of on time; the cab was left with some trash

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

Very hard to beat a British Airways international flight…the crews are always so amazing! One flight attendant that really stood out was Emma…she was very personable and accommodating with any request we had!!

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

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

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

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

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.