$121 Find Cheap Flights from Caribbean Islands to Massachusetts - Compare and Save

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 Islands to Massachusetts departing on 9/29. 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.
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Low season

January

Cheapest flight

$121
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from San Juan Airport to Hartford

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

Insights shared by verified travelers who flew the route from Caribbean Islands 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 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 airlines fly most frequently to Massachusetts?

    Caribbean Islands and Massachusetts are connected by different airlines. The airlines that fly that route the most regularly are JetBlue (97 flights per week), Icelandair (15 flights per week), and Qatar Airways (12 flights per week).

  • How many airports are there in Massachusetts?

    There are 9 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 90% 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 $327.

  • 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 $308. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $450 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 $285 on average. Morning departures are around 4% 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 $382.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Caribbean Islands found in the last 5 days was to Boston, at $178 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 $178.

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

    The cheapest month for flights from Caribbean Islands to Massachusetts is December, when tickets cost $255 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $366 and $345 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 2 weeks before departure, which saves you about 3% 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 Islands, there are direct flights to Massachusetts from 11 cities. The city with the most direct flights is San Juan, with 92 direct flights each week.

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

    There are around 26 direct flights from within Caribbean Islands to Massachusetts every day. Most flights (40%) depart in the afternoon.

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

    Each week there are around 176 direct flights from within Caribbean Islands 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 Islands to Massachusetts takes 10h 44m, covering a distance of 1734 miles. The shortest route is Nassau (NAS) to Boston (BOS) with an average flight time of 3h 23m.

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

    Each week, there are 167 medium-haul flights (3-6 hour flight duration) and 9 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 (76% of total searches to Massachusetts). The next most popular destinations are Hartford (22%) and Albany (1%). 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 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.
7.8
DeltaOverall score based on 8490 reviews
8.1Boarding
7.8Comfort
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

2.0 MediocrePreeti, Jul 2026
MCI - BOS
Read more Delta reviews

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

If you cant travel Delta One, Comfort Class is the next best thing!

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

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

The tray table was broken and the food was terrible.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

I missed my flight and had to buy new tickets Rome- Boston

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

Super friendly with lots of drink options an entertainment. Friendly crew.

I like flying first class, and United has a nice one

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

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

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

I was forced to check my carry-on backpack despite there being space - but it came out on the baggage carousel so fast it didn't even delay my pickup. Otherwise a good flight. Boarding began early (which was disadvantageous for me) but fine.

Excellent staff helping my 96 year old senior promptly with her oxygen needs

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Plane features were VERY old and outdated. footrest cushion was completely lose, plane felt dirty and a bit grimy. i was in business class. the lead flight attendant, Mary made a few announcements that didn't seem to put the cabin at ease (it didn't necessarily bother me, but could have bothered others). she said "the seat cushions aren't FDA approved, so you have to put them on after we take flight." everyone had already applied the seat cushions, and saying something isn't approved for flight may cause alarm. she also said at one point over the announcement ... "we can't get up because we are too afraid of the jet stream impacts" -- again, not helpful to those who are nervous fliers.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

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!!

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

No enough space plus only allowing one laggage instead of two like other airlines.

Qatar airways ,boarding arrangements at Hamid international airport could been better

Flight was delayed. But my finances flight with JetBlue a week before same route was extra delayed and then cancelled at 2am when his flight was suppose to take off at 7pm was never provided a hotel or anything. Came back to airport and his rescheduled flight was cancelled again for 2 days later. Was told since it was a weather issue they don’t do refunds. But that’s a lie because I booked him on another airline at the same time and they were able to take off perfectly fine

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

For whatever reason, I could not check in online. Kept getting the "It's not you it's us" message. Even when we tried the kiosk at the airport - same results. The check-in person had a very difficult time getting our boarding passes together despite the fact that we could show confirmation on the jetblue website. After a very long time we finally got boarding passes. The only other issue is, my vegetarian meal featured chicken.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

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.

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

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

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 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.