$71 Find Cheap Flights from Caribbean Islands to Massachusetts

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Good to know

Low seasonMarch
Cheapest flight$71
Best time to beat the crowds but there is an average 3% 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 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 (119 flights per week), Qatar Airways (58 flights per week), and Hawaiian Airlines (32 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 $278.

  • 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 $216. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $279 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 $217 on average. Morning departures are around 13% 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 $267.

  • 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 $112 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 $112.

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

    The cheapest month for flights from Caribbean Islands to Massachusetts is February, when tickets cost $449 (return) on average. On the other hand, the most expensive months are August and June, when the average cost of round-trip tickets is $562 and $554 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 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 192 direct flights each week.

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

    There are around 45 direct flights from within Caribbean Islands to Massachusetts every day. Most flights (55%) depart in the morning.

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

    Each week there are around 313 direct flights from within Caribbean Islands to Massachusetts. The most common day for departures is Saturday, with 19% 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 59m, covering a distance of 1736 miles. The shortest route is Nassau (NAS) to Boston (BOS) with an average flight time of 3h 22m.

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

    Each week, there are 309 medium-haul flights (3-6 hour flight duration) and 4 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 (74% of total searches to Massachusetts). The next most popular destinations are Hartford (23%) 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.
8.0
DeltaOverall score based on 7981 reviews
7.9Comfort
8.5Crew
7.9Entertainment
7.3Food
8.2Boarding
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

I found the staff to not be very attentive at all. When paying for Business Class you expect a certain type of service and that was not found. They were almost rude even

Not good , late, and long. We came home so late and spent so much time flying around and taxiing

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Had one staff that was not pleasant. Seems they are stressed with too many people to care for.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Ok. Get a different kosher caterer. The food was odd.

Food was terrible. Crew was kind but skipped over my row for providing sandwiches and beverages.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

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.

Pathetic check in experience once again. Not enough staff scheduled at bag drop or for special assistance at LHR. Really need to rethink the whole self check in procedure. The crew was good. A very decent selection of special meals in this leg as compared to the JFK-LHR leg.

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

First time on Spirit. Definitely a streamline flight but I would fly Spirit again.

The staff was excellent and I appreciated the zero tolerance for noise making electronics and the only bad part was It took forever for the luggage to get to the baggage claim. It took over 40 minutes. And Norfolk is a small airport so it was probably airport. Staff’s fault.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Offer snacks for free. You are charging for the flight for the carry on for the seat and for a snack??? Lord

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

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.

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