$105 Find Cheap Flights from Caribbean to Massachusetts

1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

Good to know

Low seasonJanuary
Cheapest flight$105
Best time to beat the crowds but there is an average 3% 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 (170 flights per week), Delta (42 flights per week), and KLM (16 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 $275.

  • 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 $277. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $353 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 $255 on average. Morning departures are around 14% 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 $335.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Caribbean found in the last 72 hours was to Boston, at $118 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 $118.

  • 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 July, when the average cost of round-trip tickets is $619 and $553 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 13% 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 16 cities. The city with the most direct flights is San Juan, with 121 direct flights each week.

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

    There are around 47 direct flights from within Caribbean to Massachusetts every day. Most flights (50%) depart in the afternoon.

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

    Each week there are around 326 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 11h 42m, covering a distance of 1742 miles. The shortest route is Nassau (NAS) to Boston (BOS) with an average flight time of 3h 20m.

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

    Each week, there are 266 medium-haul flights (3-6 hour flight duration) and 60 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 (73% of total searches to Massachusetts). The next most popular destinations are Hartford (25%) and Albany (1%). Searches for flights to Worcester (1%), 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 8437 reviews
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
7.9Comfort
Airline reviews

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

4.0 OkayAnonymous, Apr 2026
MYR - ATL
Read more Delta reviews

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

Flight team was very courteous only complaint wS the boarding process and mandatory bag check

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

It was a great flight got here on time wish they would give headphones out for free

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!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

They forced me to check my hand luggage at the gate.

Still hasn’t left. Why are you asking how it was?

On time departure and early arrival. Flight attendant very nice.

As we approached Denver, we encountered quite a bit of turbulence. I know this can sometimes be the case as I frequently fly this route but not on American. My gripe: Usually a pilot or co-pilot alerts passengers to the possibility of turbulance ahead of time. This did not occur nor did he communiucate during what was a pretty rough ride.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

Overall a good experience, however Wifi was not working on the flight.

Airlines should be prohibited from using the seats they get away with.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

Returned home with a blood clot from flight homes and the uncomfortable aircraft I was on.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

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

They canceled my flight and never told me. There was no follow up email. I had to buy another ticket the day of.

Easy to get our TSA pre check #added. Flight crew was great and entertaining and we landed early!

Flight was delayed 6plus hours Did not take flight Customer service was terrible Will never fly again and will spread how terrible you are You stink

I didnt have a flight. Kayak must be on drugs because I confirmed with spirit that I had no booked flight.

We were surprised to be charged $99 for a personal item. And of course everything offered on the flight was an additional charge. Other than that the pilot flew and landed the plane well and the attendants and fellow passengers were nice enough.

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

Gate changed multiple times. The staff seemed annoyed that we asked for water. We had to pay for the water as well.

It was a full Spirit experience. Got to witness police officers having to deboard a passenger and cost us about an hour of delay. Front seat was spacious and better than expected.

We didn't get on the flight, they canceled our flight and said there was no flights leaving this weekend and sent me our money back.

Horrible company: canceled flights and delayed flights. Spirit canceled my flight from Miami to Philadelphia the day before we were supposed to leave from Philadelphia to Miami, with no explanation. I had to rebook another flight, spending more money and instead of flying from Miami, I had to choose a flight from Fort Lauderdale because there were no direct flights available from Miami. That created additional cost. The flight with Spirit from Fort Lauderdale was scheduled to depart at 6am, so I had to wake up my 3 and 6 years old at 3am to get to the airport in time and then, at 5am while we were at the gate the delayed the flight until 7:45am with again no explanation.

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.