$87 Find Cheap Flights from Caribbean Islands to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Boston departing on 2/7. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$124
Typical prices: $110-$243
Multiple Airlines
Fri 2/13Sun 2/22
SJU - BOS • Non-stop
Cheapest one-way
$87
Typical prices: $101-$262
Frontier
Sat 2/7
SJU - BOS • 1 stop
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Flight Deals
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Flight Deals

Cheap Flights from Caribbean Islands to Boston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean Islands to Boston

Fri, Feb 13 - Sun, Feb 22
Multiple Airlines Logo
11:22 am - 2:43 pm
SJU
-
BOS
4h 21mnonstop
Multiple Airlines Logo
10:04 am - 3:00 pm
BOS
-
SJU
3h 56mnonstop
$124Multiple Airlines
Fri, Feb 13 - Sun, Feb 22
Multiple Airlines Logo
11:22 am - 2:43 pm
SJU
-
BOS
4h 21mnonstop
Multiple Airlines Logo
10:04 am - 3:00 pm
BOS
-
SJU
3h 56mnonstop
$125Multiple Airlines
Wed, Jan 21 - Sat, Jan 24
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
Delta Logo
8:55 am - 2:00 pm
BOS
-
STT
4h 05mnonstop
$224Delta
Wed, Jan 21 - Sat, Jan 24
American Airlines Logo
3:46 pm - 10:56 pm
STT
-
BOS
8h 10m1 stop
American Airlines Logo
5:15 am - 2:23 pm
BOS
-
STT
8h 08m1 stop
$233American Airlines
Thu, Feb 12 - Thu, Feb 19
American Airlines Logo
4:37 pm - 11:16 pm
STT
-
BOS
7h 39m1 stop
American Airlines Logo
5:30 am - 5:02 pm
BOS
-
STT
10h 32m1 stop
$234American Airlines
Thu, Jan 15 - Mon, Jan 19
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
Delta Logo
8:55 am - 2:00 pm
BOS
-
STT
4h 05mnonstop
$242Delta
Wed, Feb 11 - Sat, Feb 21
United Airlines Logo
1:30 am - 3:12 pm
POS
-
BOS
14h 42m2 stops
United Airlines Logo
7:48 am - 12:23 am
BOS
-
POS
15h 35m2 stops
$243United Airlines
Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
8:50 am - 5:16 pm
POS
-
BOS
9h 26m1 stop
JetBlue Logo
8:15 pm - 7:17 am
BOS
-
POS
10h 02m1 stop
$248JetBlue
Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
8:50 am - 8:03 pm
POS
-
BOS
12h 13m1 stop
JetBlue Logo
8:15 pm - 7:17 am
BOS
-
POS
10h 02m1 stop
$249JetBlue
Thu, Feb 12 - Sat, Feb 21
United Airlines Logo
1:30 am - 10:01 pm
POS
-
BOS
21h 31m2 stops
United Airlines Logo
7:48 am - 12:23 am
BOS
-
POS
15h 35m2 stops
$252United Airlines
Useful Info

Good to know

Low seasonMarch
Cheapest flight$87
Best time to beat the crowds with an average 5% drop 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 Boston

  • How does KAYAK find such low prices on flights from Caribbean Islands to Boston?

    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 Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Caribbean Islands 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 Boston?

    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 to Boston with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Boston?

    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 to Boston from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Caribbean Islands to Boston

 
Need help choosing which airline to fly with from Caribbean Islands to Boston? 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 8024 reviews
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
7.9Comfort
Airline reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

10.0 ExcellentAnonymous, Dec 2025
DCA - SEA
Read more Delta reviews

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

I went to washroom twice and once there was no toilet seat cover and the other no toilet paper at all. I don't think it was ever replenished or checked before we boarded as it was very early on in the flight.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

In Liberia airport 5 min before our departure the airport was closed for takeoff for 30 min. Upon arrival to IAH we didn’t have any available gate and waited taxing another 40 min. As a result we arrived for 1+ h later. The walkway to the passport control in IAH is about 1-2 ml long. After the passport control you have to pass the security check again. Only 3 out of 16 checkpoints were open and the line was enormously long. As a result, even though we supposed to have 2.5 hrs gap in between the flights we missed our transfer. United rebooked us for the next available flight early morning and provided free hotel and meal vouchers through.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

Sitting on the runway after we land for almost two hours! Not sure if we should blame United or Just Dumpy Vance.

Hotter than Hades in August. Why, why do crews think that in the winter when we are already dressed for cold weather we need a cabin that is 82 degrees. Even the vents were blowing hot air.

Unbelievably poor service from flight attendants. They didn’t even do water service on a four hour flight. Just disrespectful.

United is an incompetent airline. They parked the plane on the tarmac for an hour after arriving because they “didn’t have a gate available” it was actually some sort of lie because as we de planed there were approximately 9 open and manned and empty gates that we walked past. Many people on the flight missed connections for the hour long sit on the tarmac. Utterly baffling and incompetent behavior from United flight ops.

Flight was delayed. De-icing took a while. When we landed had to wait for another plane to vacate our gate. Just an overall bad experience.

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Original flight was canceled and rescheduled for the next day. Cancelation notice was sent in the middle of the night (only saw it in the morning), leaving no room to find other options. No offers to reimburse for the extra expenses or compensations. My flight to Rio on 12/12 was also delayed for 16 hours. This seems to be the new normal for AA.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Our flight was delayed 5 hours, very disorganized, bad communication, confusion. Only good thing was the crew.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

we were delayed because of some safety check that wasn't done or available

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.

They canceled the flight and didn't assist in getting a new flight on any airline. I had to spend 10 hrs in the airport after getting a ticket On Delta for twice as much. I've flown Spirit many times and this was my worst experience I've had.

The plane was supposed to leave at 12:59 Amma and another plane took us around 9:30 am. There were 7 delay announcements. We were to receive a voucher of $12 back to pay for food at any place in the airport. One passenger tried to use the voucher was denied. I did not receive the voucher for me, my son, and grandson. I went to the desk and informed them and they took my phone # and email and they told me to wait. I did and was never sent. The plane was uncomfortable, the crew was dismissive of anyone beyond the last two seats. I will NEVER fly or recommend Spirit Airlines again.

It was good. It will be nice one check Baggage cost and picking seats were free.

Sprit being a value airlines providing flights for less prices, does its basic job. Flight was on time and ride was comfortable. Its did take off and landed on time. Luggage took sometime to arrive at carousal but that could be Newark airport issue.

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

Worst every experience travelling with Family. So much delayed while going and returning both. All airlines were time except this. not sure Spirit operational issues. No recommend Spirit. It may spoil your entire trip. Rather spent extra $ and book better airlines.

Spirit cancelled my return flight the day before travel and so I had to book a last minute flight on American Airlines.

The traffic controllers had cancelled some flights, I wish they'd done it sooner so we didn't have to sit at the airport for 3 hours.

Horrible. They canceled the flight and didn’t offer much help

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

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