$71 Find Cheap Flights from Caribbean Islands to Massachusetts

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Low seasonMarch
Cheapest flight$71
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from San Juan Airport to Hartford

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 (86 flights per week), Qatar Airways (49 flights per week), and Hawaiian Airlines (22 flights per week).

  • How many airports are there in Massachusetts?

    There are 6 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 95% 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 $234.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Saturday where round-trip tickets can be as cheap as $250. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $347 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 $240 on average. Morning departures are around 24% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $298.

  • 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 $81 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 $81.

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

    The cheapest month for flights from Caribbean Islands to Massachusetts is October, when tickets cost $423 (return) on average. On the other hand, the most expensive months are August and June, when the average cost of round-trip tickets is $613 and $553 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 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 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 136 direct flights each week.

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

    There are around 34 direct flights from within Caribbean Islands 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 237 direct flights from within Caribbean Islands to Massachusetts. The most common day for departures is Saturday, with 20% 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 37m, covering a distance of 1767 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 510 medium-haul flights (3-6 hour flight duration) and 33 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 (79% of total searches to Massachusetts). The next most popular destinations are Hartford (19%) and Albany (1%). 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 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.
7.9
DeltaOverall score based on 8007 reviews
7.3Food
8.1Boarding
7.9Entertainment
8.5Crew
7.9Comfort
Airline reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

6.0 GoodJeff, Dec 2025
JFK - MIA
Read more Delta reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

For some reason, I couldn't choose my seat. The airline gave me a seat when I got there. Not happy about that. Otherwise, everything else was great!

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Movie selection is good. Crew did not understand mileage program and were no help. Sick later. Food?

Staff on board was excellent. Positive upbeat helpful- like it used to be.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

For an expensive flight to another country, United has a lot of nerve serving pretzels and no meals (unless, of course, you want to buy something to eat). Unacceptable.

The food is terrible. The same pasta or chicken with bad taste and presentation

United have really come back. Airport and boarding process is clear and good, app and information also very good

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

It was probably one of the worst flights I’ve been on. The restrooms were never cleaned or stocked. The food was very subpar, and i usually enjoy airline food, so I was disappointed. It was just all around a bad experience. The only saving grace was the flight attendants.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Qatar Airways only had spicy meals on the menu in economy class. You might want to get food in the airport before boarding.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Flight was in time, very smooth ride and surprisingly lots of legroom in the cabin so I certainly will fly with spirit again

The seats are the most uncomfortable seats I’ve ever sat in. Don’t believe I’ll ever fly spirit again!!

Seats Are hard, Plane was very dirty, used gum stuck on my tray table, wet red liquid under my feet at me seat

Seats are too close. Bags are too expensive. One bag should always be free.

Flight was canceled and instead of rescheduling at the gate we had to go out to the ticket counter. Unruly kids kicking the back of my rows chair with staff to inattentive to say something.

Customer feedback I sent to Spirited today: “I will never fly Spirit Airlines again and will work hard to convince my friends and family to boycott/avoid Spirit Airlines at all costs. I booked three seats for me and my 8 and 10 year old children on NK 1222 from Orlando to Kansas City for 12/7/25 leaving Orlando at 10:37AM. This itinerary was abandoned by Spirit and we were rebooked onto Spirit flight NK 213 leaving at 9:06PM without any notice. Then the nightmare really began. Flight 213 was delayed a total of 12 times, finally leaving at 6:35AM the following day. The gate was changed 5 times and our electronic boarding passes were invalidated at midnight. The worst part was that the 12 separate delays were incremental making it impossible to plan for accommodations for my family. My kids missed a day of school and barely slept under the harsh lights with lots of noise on the filthy airport floor. The customer service agent at Spirit Airlines told us we would be emailed a voucher for a hotel which never happened. I asked about it multiple times and it never arrived in my email inbox. This whole unfortunate situation could’ve been avoided if spirit had taken a realistic approach and delayed the flight from 9 PM until 6 AM from the beginning. My son gleefully deleted the Spirit app from my phone once we landed and we will never fly with Spirit again.”

The experience was really good, the crew members were excellent

Honestly horrible. The plane on the way back was delayed 6 times with no explanation on why. When I asked for a refund or some money back because I had to miss a day of work because of the desk, they told me no. Because of how poorly it was handled I will most likely never take spirit again

I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta

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.