$118 Find Cheap Flights from Caribbean to Massachusetts

1 adult
1 adult, Economy

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 22% 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 seasonMarch
Cheapest flight$118
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from San Juan to Albany

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 (47 flights per week), Qatar Airways (33 flights per week), and Hawaiian Airlines (11 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 92% 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 $292.

  • 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 $233. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $298 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 $233 on average. Morning departures are around 2% 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 $272.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Caribbean found in the last 72 hours was to Boston, at $136 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 $136.

  • 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 $452 (return) on average. On the other hand, the most expensive months are August and January, when the average cost of round-trip tickets is $613 and $554 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

  • How many cities have direct flights to Massachusetts?

    From Caribbean, there are direct flights to Massachusetts from 7 cities. The city with the most direct flights is San Juan, with 68 direct flights each week.

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

    There are around 19 direct flights from within Caribbean to Massachusetts every day. Most flights (61%) depart in the afternoon.

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

    Each week there are around 133 direct flights from within Caribbean to Massachusetts. The most common day for departures is Sunday, 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 10h 34m, covering a distance of 1761 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?

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Massachusetts. Instead, there are 133 medium-haul flights (3-6 hour flight duration), with the most arriving from San Juan.

  • 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 (18%) and Albany (2%). 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 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 7957 reviews
7.9Entertainment
7.3Food
7.9Comfort
8.5Crew
8.2Boarding
Airline reviews

Awful. Flight from Cape Town was cancelled, rebooked for another day through Johannesburg, was downgraded to economy

4.0 OkayOlaf, Sep 2025JNB - ATL
Read more Delta reviews

Awful. Flight from Cape Town was cancelled, rebooked for another day through Johannesburg, was downgraded to economy

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

The airport crew helped a lot, what I didn’t like? We were not informed that we needed to pick our luggage’s, if the crew at the luggage center didn’t tell me I would have been home without my belongings, I was heading out to my next connecting flight while looking for what gate to go to, I asked one of the crews for help, he told me and he also told me to not forget to grab my luggage’s which was chocking, because on my way out the country that wasn’t required, I just hope none of your customers lost their luggage’s because of this.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

The flight crew was friendly. I tried to adjust my seat online ahead of time but no option existed without additional fees. My friend asked at the gate about a seat change and was able to make it happen. That was great! The flight crew moved a very tall gentleman and his companion which allowed us to have more space which was nice. Overall, good experience. Appreciated the blanket and pillow.

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

The delayed flight was awful and moving the departure gate twice was annoying

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

The flight was on time and crew were nice, seats were tight and there was entertainment available

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

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

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

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.

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

The flight was canceled leaving us scrambling to find another airline. I should have known not to trust Spirit

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.