$90 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
$109
Overall average: $169
Spirit Airlines
Thu 2/5Sun 2/8
SJU - BOS • Non-stop
Cheapest non-stop
$104
Typical prices: $139-$292
Spirit Airlines
Fri 1/30Mon 2/2
SJU - BOS • Non-stop
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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

Thu, Feb 5 - Sun, Feb 8
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
$109Spirit Airlines
Fri, Feb 13 - Mon, Feb 23
Frontier Logo
6:00 am - 9:19 am
SJU
-
BOS
4h 19mnonstop
Frontier Logo
10:04 am - 3:00 pm
BOS
-
SJU
3h 56mnonstop
$116Frontier
Wed, Mar 4 - Wed, Mar 11
Delta Logo
4:15 pm - 1:09 am
STT
-
BOS
9h 54m
1 stop
Delta Logo
8:40 am - 12:43 pm
BOS
-
STT
4h 03mnonstop
$228Delta
Wed, Mar 4 - Wed, Mar 11
Delta Logo
4:15 pm - 1:09 am
STT
-
BOS
9h 54m
1 stop
Delta Logo
6:00 am - 1:00 pm
BOS
-
STT
7h 00m
1 stop
$232Delta
Mon, Mar 16 - Sun, Mar 22
American Airlines Logo
5:25 pm - 10:02 am
STT
-
BOS
16h 37m
1 stop
American Airlines Logo
5:40 am - 12:16 pm
BOS
-
STT
6h 36m
1 stop
$243American Airlines
Mon, Mar 16 - Sun, Mar 22
JetBlue Logo
2:41 pm - 8:29 pm
STT
-
BOS
5h 48m
1 stop
JetBlue Logo
9:13 am - 1:17 pm
BOS
-
STT
4h 04mnonstop
$258JetBlue
Fri, May 1 - Tue, May 12
United Airlines Logo
12:30 am - 9:59 pm
POS
-
BOS
21h 29m
2 stops
United Airlines Logo
10:00 am - 11:23 pm
BOS
-
POS
13h 23m
2 stops
$266United Airlines
Fri, Feb 13 - Sat, Feb 21
JetBlue Logo
8:50 am - 5:16 pm
POS
-
BOS
9h 26m
1 stop
JetBlue Logo
8:15 pm - 7:17 am
BOS
-
POS
10h 02m
1 stop
$271JetBlue
Thu, Feb 12 - Sat, Feb 21
United Airlines Logo
1:30 am - 11:57 pm
POS
-
BOS
23h 27m
2 stops
United Airlines Logo
7:48 am - 12:23 am
BOS
-
POS
15h 35m
2 stops
$276United Airlines
Sat, May 2 - Tue, May 12
American Airlines Logo
3:47 pm - 11:12 am
POS
-
BOS
19h 25m
2 stops
American Airlines Logo
4:01 pm - 2:32 pm
BOS
-
POS
22h 31m
2 stops
$292American Airlines
Useful Info

Good to know

Low seasonMarch
Cheapest flight$90
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 8% 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 8087 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

4.0 OkayJohn, Jan 2026
DAL - ATL
Read more Delta reviews

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

My requested wheelchair never appeared. So many entertainment choices yet, I found little of interest and no internet option to search on my own. Both were minor issues.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Mean flight attendant. I wanted to reuse my plastic cup, but he (Matthew) said he can't for safety. I then said "I don't want water then" and he poured me a glass. I hope Matthew gets herpes and spends the rest of his life poor, lonely, and homeless.

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The seats were comfortable and we had leg room. Great entertainment.

The flight crew where really good. Better then the crew from BNE to SFO

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Safe made to destination. Late to start at GVA for icy reasons but we fought our next fly.

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

No enough space plus only allowing one laggage instead of two like other airlines.

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The comfort of Business Class made this trip far more comfortable. I was indeed surprised when I asked one of the flight attendant to help me set up my "bed", she responded that "We don't make beds in Business Class any longer...only First Class" I believe her name was Giselle, but I'm not certain. She did instruct me how to adjust the seat, place the hooded cover and I clearly understood how to place the blanket and the cover. Additionally, the meal I was served (a beef dish) was almost inedible. The beef was tough and odd tasting. I didn't mention it as I was hoping to quickly settle down and try to get some sleep.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

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.

Horribly late because they had no crew!!! And then jet bridge didn’t work!! Then we arrived at a gate at lax miles away that we had to take a shuttle to a terminal!! I was over 3 hours late to getting the LA! Should have been here at 8:30 and at an appointment at 10:30 and arrived and left lax at 11 am!! Horrible experience!!!

Extra legroom with my upgrade bundle. Clean aircraft, on-time departure, early arrival. Good value for the price.

I didn't have a flight because of a ticking problem that was discovered at the airport at checkin for the initial flight of the round trip.

Even though the plane was delayed from the previous airport, the staff recognized this and kept us informed. The flight crew was absolutely awesome from on my flight from Ft. Meyers to AC. Great experience all around!

Flight was delayed would have liked it to have been on time. I didn't experience the food or entertainment but the boarding process was smooth and the flight crew worked well together and did a great job!

Not seat assigned because overbooking. We could go because some people decided to give their seats.

Spirit loves to pick and choose when to harass you about your personal item. I’ve flown numerous times with the same bag with no problem yet flying out of Orlando they forced me to pay $99 for a carry on and then ran out of overhead space. Do better!

For the price of the fare, there really isn’t much to complain about.

didn't order food on board. there's no way to hold a water botton on the way. otherwise it was a pleasant flight, thanks to the crew.

Even though there was a delay the crew was exceptional.

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