$88 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 1/14. 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
$119
Typical prices: $111-$245
Multiple Airlines
Sat 2/14Mon 2/23
SJU - BOS • Non-stop
Cheapest one-way
$88
Typical prices: $150-$322
Spirit Airlines
Wed 1/14
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

Sat, Feb 14 - Mon, Feb 23
Multiple Airlines Logo
6:00 am - 9:19 am
SJU
-
BOS
4h 19mnonstop
Multiple Airlines Logo
8:01 pm - 1:08 am
BOS
-
SJU
4h 07mnonstop
$119Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
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
$134Multiple Airlines
Wed, Feb 18 - Mon, Feb 23
American Airlines Logo
1:16 pm - 11:20 pm
STT
-
BOS
11h 04m2 stops
American Airlines Logo
6:00 am - 3:49 pm
BOS
-
STT
8h 49m2 stops
$233American Airlines
Fri, Feb 13 - Thu, Feb 19
United Airlines Logo
1:30 am - 2:30 pm
POS
-
BOS
14h 00m2 stops
United Airlines Logo
7:15 am - 1:05 am
BOS
-
POS
16h 50m2 stops
$242United Airlines
Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
8:50 am - 8:03 pm
POS
-
BOS
12h 13m1 stop
JetBlue Logo
6:15 pm - 7:17 am
BOS
-
POS
12h 02m1 stop
$248JetBlue
Thu, Feb 12 - Sat, Feb 21
United Airlines Logo
1:30 am - 9:31 pm
POS
-
BOS
21h 01m1 stop
United Airlines Logo
7:48 am - 12:23 am
BOS
-
POS
15h 35m2 stops
$252United Airlines
Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
12:22 pm - 8:03 pm
POS
-
BOS
8h 41m1 stop
JetBlue Logo
8:15 pm - 10:57 am
BOS
-
POS
13h 42m1 stop
$263JetBlue
Fri, Feb 13 - Sat, Feb 21
American Airlines Logo
4:40 pm - 10:09 am
POS
-
BOS
18h 29m2 stops
American Airlines Logo
5:00 pm - 3:39 pm
BOS
-
POS
21h 39m2 stops
$291American Airlines
Sat, Jan 17 - Sat, Jan 24
Delta Logo
3:25 pm - 7:40 pm
MBJ
-
BOS
4h 15mnonstop
Delta Logo
9:25 am - 1:56 pm
BOS
-
MBJ
4h 31mnonstop
$300Delta
Sat, Jan 10 - Sat, Jan 17
Delta Logo
2:40 pm - 6:08 pm
NAS
-
BOS
3h 28mnonstop
Delta Logo
11:12 am - 5:00 pm
BOS
-
NAS
5h 48m1 stop
$305Delta
Useful Info

Good to know

Low seasonMarch
Cheapest flight$88
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 8014 reviews
7.3Food
7.9Comfort
8.5Crew
8.1Boarding
7.9Entertainment
Airline reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

2.0 MediocrePeter, Dec 2025
JFK - MEM
Read more Delta reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Premium economy is like the forgotten class. Aside from meal service never saw a flight attendant. Any additional beverages required going to the very back of the plane to request and there was rarely an attendant there. Seat leg / foot rest hardly elevates and not well suite for someone under 5’6. Bulky armrests

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Delta One upgrade it would have been great if my tray extended (it was jammed and wouldn’t pull out), seatbelt had too much slack & my little cabin door didn’t close properly

I paid for a business class ticket on Delta. It was sourced to Virgin Atlantic. They changed out the aircraft which had fewer upper class tickets. Even though I'd checked into the lounge, was receiving alerts via kayak about the delay and changes; no one informed me that the seat would be changed - until I attempted to board and was told that I would have an economy seat or they could search to put me on another airline. Even the flight crew were informed of this change (10 passengers were bumped out of Upper Class) around 2 pm (1400) time. Hours would have helped to consider alternatives instead of making a last minute change. There needs to be compensation from both Delta and Virgin given this change in service/experience.

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Every single flight that we got on was delayed by several hours or more. I honestly didn’t think we would get out of Atlanta because our flight was supposed to leave at 7:59 and it kept getting kicked back further and further. Delta stands for Don’t Ever Leave The Airport!

Great. I had to modify a flight. That was easy and free. Thank You

The flight was delayed for 1:30 hours for maintenance issues. They should give more information about connecting flights. For a Business Cabin the Crew was mediocre.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

Flight was late - I was downgraded from first class to coach

Not good - outbound flight was delayed and missed my connection even though I got to the gate after running through the airport - the agent would not let me on because the door was closed (flight had not left). There was no notification from United - overall experience was very disappointing. Additionally, I was downgraded from first class to coach on the alternative flight

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

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

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

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.

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.

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.

Spirit cancelled the flight very late last night, I was on the way to the airport when I found out

First time in a decade I threw up on the flight, turbulence was terrible!! The staff were kinda rude at times.

Boarding was good, clearly explained and efficient. Staff were helpful, I would've liked a place to get coffee that wasn't Starbucks

I really liked the personalized treatment at the MDE airport, where someone from SPIRIT received me at the entrance of the counter line to ask if the weight of my luggage was accurate or if I wanted a better seat, gave me a name tag for my luggage and walked me to the counter. Thank you.

The most horrible flight ever not only Spirit delayed our flight 2 hours departure time for a 1 hour flight — that I could have driven FLL to TPA and spend less time on the road —- and they did the same on the return with 2-hr delay again!!! Then to top all, the rubber like and most unconfortable seats in the industry with no leg room!!! There should be an award for these kinds of companies measuring % of returning customers!!!

I can't rate food or entertainment when previously you know the lowest rate doesn't have any of that included. However I want to congratulate the crew and specially the flight attendants for their kindness and free smile even knowing is the end of a long day. I had the opportunity to chat to Hailey, Despise her busy job, she had the time to chat with me and even when she asked me to stop using my phone, not with words but with her sweet face expression, was as MasterCard said, a priceless moment. She even told me she learned from the best teacher, her Mom Ruth, a flight attendant working in the same flight, Definitely, with people like them, the real Americans, this country will overcome the worst moment in USA history falling in the hands of the biggest senil Psycho felon. God bless America!!!!

The flight was cancelled and Spirit said they could not rebook me on another flight for six days. They said they couldn't do anything for another six days.

Flight was on time, Newark staff, especially Nathan, very helpful, and plane crew to RDU very good without being pushy. We arrived early, and had a gentle landing.

See my last comment for the first leg. That should’ve been in here

Horrible. Arrived at my gate at 6:37 for a 6:50 flight and was denied by staff to board. Literally watched my flight leave from the window and it didn’t take off until after 7am. Tried to talk to staff and they were rude beyond compare. Will never fly with this airline again.

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