$114 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 12/24. 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.
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1 adult, Economy, 0 bags

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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

Tue, Dec 23 - Sun, Jan 11
Frontier Logo
4:19 pm - 1:24 amSJU-BOS
10h 05m1 stop
Frontier Logo
12:43 pm - 5:47 pmBOS-SJU
4h 04mnonstop
$185Frontier
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Sat, Dec 20 - Tue, Dec 30
Multiple Airlines Logo
3:15 pm - 6:39 pmSJU-BOS
4h 24mnonstop
Multiple Airlines Logo
6:00 am - 1:06 amBOS-SJU
42h 06m2 stops
$186Multiple Airlines
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Fri, Dec 5 - Sat, Dec 6
American Airlines Logo
6:42 pm - 12:59 amSJU-BOS
7h 17m1 stop
American Airlines Logo
12:18 pm - 10:05 pmBOS-SJU
8h 47m2 stops
$195American Airlines
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Wed, Jan 28 - Sun, Feb 1
Spirit Airlines Logo
5:27 pm - 8:34 pmSJU-BOS
4h 07mnonstop
Spirit Airlines Logo
9:39 pm - 9:52 amBOS-SJU
11h 13m1 stop
$196Spirit Airlines
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Fri, Dec 5 - Sat, Dec 6
American Airlines Logo
2:36 pm - 12:59 amSJU-BOS
11h 23m1 stop
American Airlines Logo
12:18 pm - 10:05 pmBOS-SJU
8h 47m2 stops
$200American Airlines
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Sun, Dec 21 - Fri, Jan 2
Spirit Airlines Logo
3:15 pm - 6:39 pmSJU-BOS
4h 24mnonstop
Spirit Airlines Logo
7:34 pm - 12:41 amBOS-SJU
4h 07mnonstop
$207Spirit Airlines
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Mon, Dec 22 - Wed, Dec 31
JetBlue Logo
5:18 pm - 8:32 pmSJU-BOS
4h 14mnonstop
JetBlue Logo
6:50 pm - 11:56 pmBOS-SJU
4h 06mnonstop
$241JetBlue
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Mon, Dec 22 - Wed, Dec 31
Delta Logo
2:34 pm - 5:56 pmSTT-BOS
4h 22mnonstop
Delta Logo
8:20 am - 1:24 pmBOS-STT
4h 04mnonstop
$245Delta
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Tue, Mar 31 - Thu, Apr 9
JetBlue Logo
5:15 am - 9:23 amSJU-BOS
4h 08mnonstop
JetBlue Logo
8:15 pm - 12:15 amBOS-SJU
4h 00mnonstop
$246JetBlue
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Sun, Dec 21 - Tue, Dec 30
Delta Logo
4:15 pm - 8:27 pmMBJ-BOS
4h 12mnonstop
Delta Logo
6:40 am - 8:41 pmBOS-MBJ
14h 01m1 stop
$321Delta
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Everything you should know

Cheapest round-trip
$185
Typical prices: $123-$278
Frontier
Tue 12/23Sun 1/11
SJU - BOS • 1 stop
Cheapest non-stop
$190
Typical prices: $148-$289
Frontier
Sat 2/28Sun 3/1
SJU - BOS • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Useful Info

Good to know

Low seasonMarch
Cheapest flight$114
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Saint Thomas Island 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 7996 reviews
7.3Food
7.9Entertainment
7.9Comfort
8.5Crew
8.2Boarding
Airline reviews

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

8.0 ExcellentBobby, Oct 2025GSP - ATL
Read more Delta reviews

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

Seats comfortable, service and food very mediocre, staff not very attentive, worse than many other our flights with Delta.

Overall good experience; however, there was one flight attendant who was rather rough compared to everyone else. Everything else was good: entertainment, food. Delta keeps on delivering! Thank you!

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Flight left on time. Boarding was easy. Arrived to EWR 30 mins early. Luggage was deplaned in good time. Overall a very good experience.

Flight from Rome to SFO was excellent compared To our flight to Europe from SFO. The food was much tastier. You can see how UNITED is skimping, though. Instead of getting something mid flight you had to ask for it. It was not automatically served. There was a cookie at the end of the arrival meal, for example that tasted like it just came out of a box. They used to serve a little container of nuts, now … a tiny container of nuts, mixed with pretzels. This was business class that you really have to pay for! But this is minor complaints compared to the overall. My major complaint is the position of the even numbered seats by the windows. You have to turn around to see your window & the positioning as some other controls are harder to get at. This is compared to the odd number seat that are perfectly aligned.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

Excellent all round, first time flying United. App is very helpful.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Nice comfortable flight from Barcelona back to the states. The premium economy offers the extra room we need for my husband. The food was good and our flight attendants were excellent.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

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.

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

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

The gate agents for spirit at EWR wouldn’t give me my ticket to board when I arrived 50 min from the flight, saying that I wouldn’t make my flight. They tried to reschedule me to arrive at my destination 14 hours after the original flight, which included a 10 hr layover in another city. I rebooked with another airline and it took me a total of 5 min to go through security. Then I see a charge on my card for a $100 change fee that I did not approve. Beware of this horrible place and these horrible people

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

Waited at the airport for over 4 hours to board this flight. Terrible airline

Was supposed to take off 8:00 last night. Got delayed till 8:00 this morning

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

When the flight ticket is expensive and you have to purchase check in luggage and there is no snacks, no entertainment, tight seats stuffed in the back of the plane not such good experience. I would like some to reach out to me . I paid for check luggage when I bought the ticket they made me pay again on the return flight extra $70. Very frustrating.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

They didn't let me board with a proper boarding pass. I threw away my bags so that I can board and was defined boarding. Had to take the next flight after paying more.

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