$93 Find Cheap Flights from Caribbean 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 2/24. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$119
Overall average: $205
Spirit Airlines
Wed 2/25Sat 2/28
SJU - BOS • Non-stop
Cheapest one-way
$93
Typical prices: $117-$275
Frontier
Tue 2/24
SJU - BOS • 1 stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Boston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean 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 to Boston

Wed, Feb 25 - Sat, Feb 28
Spirit Airlines Logo
3:30 pm - 6:56 pm
SJU
-
BOS
4h 26mnonstop
Spirit Airlines Logo
8:01 pm - 1:08 am
BOS
-
SJU
4h 07mnonstop
$119Spirit Airlines
Thu, Feb 26 - 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
$120Multiple Airlines
Thu, Mar 26 - Fri, Apr 3
JetBlue Logo
3:20 pm - 8:24 pm
AUA
-
BOS
5h 04mnonstop
JetBlue Logo
6:30 am - 11:10 am
BOS
-
AUA
4h 40mnonstop
$230JetBlue
Wed, Mar 25 - Mon, Mar 30
JetBlue Logo
2:41 pm - 8:29 pm
STT
-
BOS
5h 48m
1 stop
JetBlue Logo
9:00 am - 1:04 pm
BOS
-
STT
4h 04mnonstop
$240JetBlue
Wed, Apr 22 - Mon, Apr 27
United Airlines Logo
4:30 pm - 1:29 pm
AUA
-
BOS
20h 59m
2 stops
United Airlines Logo
6:00 am - 2:00 pm
BOS
-
AUA
8h 00m
1 stop
$242United Airlines
Wed, Mar 25 - Sun, Mar 29
Delta Logo
3:55 pm - 10:54 pm
STT
-
BOS
6h 59m
1 stop
Delta Logo
8:40 am - 12:43 pm
BOS
-
STT
4h 03mnonstop
$246Delta
Fri, Apr 17 - Wed, Apr 22
American Airlines Logo
1:15 pm - 11:07 pm
STT
-
BOS
9h 52m
1 stop
American Airlines Logo
6:53 pm - 10:47 am
BOS
-
STT
15h 54m
1 stop
$250American Airlines
Thu, Apr 30 - Sat, May 2
United Airlines Logo
4:30 pm - 9:25 am
AUA
-
BOS
16h 55m
2 stops
United Airlines Logo
10:00 am - 12:40 pm
BOS
-
AUA
26h 40m
2 stops
$262United Airlines
Thu, Mar 5 - Sat, Mar 7
American Airlines Logo
3:21 pm - 10:40 pm
SXM
-
BOS
8h 19m
1 stop
American Airlines Logo
5:30 pm - 11:29 am
BOS
-
SXM
16h 59m
2 stops
$284American Airlines
Thu, Mar 12 - Wed, Mar 18
Delta Logo
3:20 pm - 7:15 am
SXM
-
BOS
15h 55m
1 stop
Delta Logo
5:35 am - 1:54 pm
BOS
-
SXM
8h 19m
1 stop
$306Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$93
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from San Juan Airport to Boston

Flights from Caribbean to Boston: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Caribbean to Boston 
JasmaryFlew with Spirit Airlines
SJU
-
BOS
Feb 2026
I would advice passengers to bring their own snack as most items are out of stock
slovely08Flew with JetBlue
AUA
-
BOS
Dec 2024
Be prepared for long security times, you have to clear customs in Aruba, and there can be a substantial line if you get there at the wrong time. They tell you to be there 3 hours early for a reason.

FAQs for booking flights from Caribbean to Boston

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Caribbean 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 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 with another airline.

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

 
Need help choosing which airline to fly with from Caribbean 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 8203 reviews
7.2Food
7.8Entertainment
7.9Comfort
8.5Crew
8.1Boarding
Airline reviews

Awful - both legs. The check in was awful, getting on the plane required walking down a spiral staircase (dangerous), then taking a bus about 5 miles out from the terminal. The seat was broken (I was in business), there was no internet during the flight (both legs). The aircraft was very old. I saw rust in some place, tape holding things up in the bathroom. This was an unacceptable experience for such a long haul flight.

2.0 MediocreShebani, Feb 2026
CDG - SFO
Read more Delta reviews

Awful - both legs. The check in was awful, getting on the plane required walking down a spiral staircase (dangerous), then taking a bus about 5 miles out from the terminal. The seat was broken (I was in business), there was no internet during the flight (both legs). The aircraft was very old. I saw rust in some place, tape holding things up in the bathroom. This was an unacceptable experience for such a long haul flight.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

bulkhead seat had very little legroom - even in bsiness class.

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

Both of my flights arrived early and check in process was smooth

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.

The gates should be ready when we land. Waiting on the runway for a hour is ridiculous.

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Very smooth flight, good legroom with the "even more room" seats. Entertainment choice was excellent, wifi on board, plane was modern. Pilot got a round of applause for a smooth landing in very blustery conditions. Love flying with them. Check in was OK too. We were too early so we had to wait until groundstaff showed up 3hrs before the flight.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

They initially informed us that the flight was delayed, but only after waiting an hour for updates. In any event, the flight was canceled, but the way it was handled was really poor and egregious. I feel they handled the situation of informing travelers very irresponsibly. I sat in a wheelchair at the airport for over four hours before finally being told that the flight was canceled.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

The flight from Boston to San Juan was boring since you guys don’t offer wings if during the flight. The returning flight was better offering WiFi to passengers. The food was horrible not enough on stock.serve paying customers better.

There absolutely needs to be WiFi on flights. Not sure why this new aircraft did not have the capability, but it made for a very frustrating flight. I honestly would have paid twice as much for another airline to have WiFi as an option, especially as a mom with kids who have disabilities.

More comfortable seats, free snacks and soft drinks, some sort of entertainment or WiFi.

Delay at the gate without any communication such as announcement, sign, monitor, email or text. Found out later we were boarded with the knowledge of a significant delay, awaiting communication from Europe. Pilot was the only source of information regarding the delay after a long gate delay and sitting for more than 30 minutes after boarding. More than 2 hour delay, landing at 2 AM. Offered to deplane and reboard, but probably should have just waited rather than repeat the process. Not the first time experiencing the lack of communication with Spirit airlines. This morning was not as bad as showing up to a terminal without an agent (or aircraft) without any sort of communication. Much later an email was sent that stated our flight was rescheduled for a week later. Situations do arise, but simple communication can alleviate a lot of the frustration. Hard to believe a corporation doesn't understand that. But, you get what you pay for...

This was a horrible experience for both KAYAK and Spirit. My flight was canceled with no alternative flight option. I paid $600 for a last minute flight and didn't receive an email from KAYAK regarding the cancelled flight until hours after it was canceled. Never again for either.

No complaints with pricing so don’t expect a lot of extras.

Flight out was great but this flight was canceled and nothing was available for 2 days after this so I had to purchase an expensive ticket from another airline so I could go home. The flight cancellation was said to be a crew issue, it wasn’t weather or maintenance.

Flight got cancelled 1.5 hours prior to gate open and logistics of travel got delayed.

They cancelled the flight due to crew unavailability. The next day they cancelled the flight again.

Forgot my anxiety pills, crew didn’t knew what to do then few minutes after they gave me a bottle of water and told me to walk thru the hall. They should be trained for this kinds of situations cause it really would help someone. Tips: bottle of water (airports should allow passengers at least having them thru) for this kinds of situations. Alcohol wipes just in case they don’t have. Tap water on skin (preferably little cold or a normal temperature) this will help.

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