$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 1/13. 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
$134
Overall average: $161
Multiple Airlines
Fri 2/27Mon 3/2
SJU - BOS • Non-stop
Cheapest one-way
$88
Typical prices: $150-$322
Spirit Airlines
Tue 1/13
SJU - BOS • 1 stop
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Flight Deals
Useful Info
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 27 - Mon, Mar 2
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
Fri, Jan 23 - Mon, Jan 26
Spirit Airlines Logo
10:52 am - 2:12 pm
SJU
-
BOS
4h 20mnonstop
Spirit Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
$135Spirit Airlines
Mon, Mar 16 - Tue, Mar 24
JetBlue Logo
2:41 pm - 8:34 pm
STT
-
BOS
5h 53m1 stop
JetBlue Logo
9:45 am - 1:46 pm
BOS
-
STT
4h 01mnonstop
$224JetBlue
Tue, Feb 3 - Tue, Feb 10
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
Delta Logo
6:00 am - 1:22 pm
BOS
-
STT
6h 22m1 stop
$229Delta
Tue, Feb 3 - Tue, Feb 10
Delta Logo
4:15 pm - 1:04 am
STT
-
BOS
9h 49m1 stop
Delta Logo
8:00 am - 4:20 pm
BOS
-
STT
7h 20m1 stop
$233Delta
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
$242JetBlue
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
Tue, Feb 10 - Tue, Feb 17
American Airlines Logo
8:50 am - 5:25 pm
GCM
-
BOS
8h 35m1 stop
American Airlines Logo
5:25 am - 3:25 pm
BOS
-
GCM
10h 00m1 stop
$284American Airlines
Tue, Feb 10 - Tue, Feb 17
American Airlines Logo
8:50 am - 8:11 pm
GCM
-
BOS
11h 21m2 stops
American Airlines Logo
5:25 am - 3:25 pm
BOS
-
GCM
10h 00m1 stop
$289American Airlines
Sat, Jan 17 - Thu, Jan 22
United Airlines Logo
2:25 pm - 9:57 pm
GCM
-
BOS
7h 32m1 stop
United Airlines Logo
7:07 pm - 1:45 pm
BOS
-
GCM
18h 38m2 stops
$291United Airlines
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 8019 reviews
8.1Boarding
7.9Entertainment
7.9Comfort
8.5Crew
7.3Food
Airline reviews

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

6.0 GoodAnonymous, Dec 2025
BOS - MSP
Read more Delta reviews

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

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

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

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

It was good, although we could not get our preferred seats, we did enjoy the whole experience from Costa Rica. I still don't understand why our luggage is not the first to come out at the band.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

everything was pretty good. Houston airport is awful. Unnecessarily inefficient; people working there are rude. Badly run

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

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

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.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

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. :)

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.

Delays due to a "power bank removal", no wifi, pilot said wrong arrival city, stewardess mumbled the word drinks as she rushed past, loud passengers with no enforcement of rules (blasting music out loud on their phones), screaming children

They cancelled my flight same day with no explanation why. They offered to rebook me but it would not be until 2 days later. I will never use them again.

Flight was cancelled with no help From spirit or kayak. Please refund asap

The flight was delayed by over an hour. The flight departure time and gate info kept changing several times. Very frustrating boarding experience and inconvenient for families with little children.

I waited for 4+ extra hours to even board when i was fighting off a cold. So i was sitting there in the airport with a fever and chills while spirit wasted my time. Then once on the plane we had at least an extra hour of taxiing before and after takeoff. Really poor airline, no amenities to speak of, and a lack of organization that will just ruin your experience.

Got to LAX at 3:20 am, the counter personnel did not start to check in bags till 3:40 am. I patiently waited at the priority check in line as they started to take people from the general line. After about 15 minutes of waiting, I approached the lady exactly in front of the priority line and asked her if they would be taking people from the priority line or if I would need to switch to waiting in the general line. She responded “yes”, I then asked her yes to what? And she yelled back at me loudly “I SAID YES!” Needless to say, I waited at the end of the line of the general line. I could have been told the priority line would not be called upon and could have queued in the general line ahead of many people that arrived to cue after I did

Very bad. Our flight was canceled and we need to rebook another flight which was in two hours after we’ve known about cancelation. It changed our plans. We had financial and other loses. Nobody did reimbursement to us.

A flight attendant was extremely friendly and offered to move me to a row that was less crowded

Awful!!! Spirit cancelled my flight just 4 hours before departure- with no alternative flights available. I ended up missing a huge family gathering because I wasn’t able to get out. Such An awful experience. And on top of that, all the buckle and dime-ing for bags. I will never book with Spirit EVER

Spirit has improved a lot since I flew with it in 2011. I give the airline a huge thumbs up!!

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