$77 Find Cheap Flights from Boston to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Caribbean Islands departing on 6/21. 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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KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Caribbean Islands.
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Flights Deals

Best Caribbean Islands Flight Deals from Boston

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$264
Santo Domingo
Santo Domingo1 stop$314
Montego Bay
Montego Bay1 stop$271
Oranjestad
Oranjestad1 stop$278
Nassau
Nassaunonstop$360
Kingston
Kingston1 stop$306
Simpson Bay
Simpson Bay1 stop$332
Providenciales
Providenciales2 stops$367
Bridgetown
Bridgetown1 stop$393
Port of Spain
Port of Spain2 stops$417
George Town
George Town2 stops$420
Willemstad
Willemstad2 stops$425
Castries
Castries2 stops$789
St. John's
St. John's1 stop$509
Puerto Plata
Puerto Plata1 stop$365
Aguadilla
Aguadilla1 stop$309
Punta Cana
Punta Cana1 stop$264
Santo Domingo
Santo Domingo1 stop$314
Montego Bay
Montego Bay1 stop$271
Oranjestad
Oranjestad1 stop$278
Nassau
Nassaunonstop$360
Kingston
Kingston1 stop$306
Simpson Bay
Simpson Bay1 stop$332
Providenciales
Providenciales2 stops$367
Bridgetown
Bridgetown1 stop$393
Port of Spain
Port of Spain2 stops$417
George Town
George Town2 stops$420
Willemstad
Willemstad2 stops$425
Castries
Castries2 stops$789
St. John's
St. John's1 stop$509
Puerto Plata
Puerto Plata1 stop$365
Aguadilla
Aguadilla1 stop$309

Cheap Flights from Boston to Caribbean Islands

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

Recent round-trip flight deals from Boston to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Boston to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
4:40 pm - 1:11 amBOS-SJU
8h 31m1 stop
Spirit Airlines Logo
12:55 pm - 11:29 pmSJU-BOS
10h 34m1 stop
$155Spirit Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
Spirit Airlines Logo
9:46 am - 8:02 pmBOS-SJU
10h 16m1 stop
Spirit Airlines Logo
1:59 am - 9:09 amSJU-BOS
7h 10m1 stop
$170Spirit Airlines
Find Deal
Thu, May 29 - Tue, Jun 3
American Airlines Logo
11:23 am - 8:10 pmBOS-SJU
8h 47m2 stops
American Airlines Logo
12:00 pm - 12:19 amSJU-BOS
12h 19m1 stop
$223American Airlines
Find Deal
Wed, Oct 1 - Mon, Oct 6
Delta Logo
8:10 am - 12:15 pmBOS-SJU
4h 05mnonstop
Delta Logo
1:27 pm - 5:39 pmSJU-BOS
4h 12mnonstop
$224Delta
Find Deal
Sat, Sep 13 - Wed, Sep 17
United Airlines Logo
5:30 am - 12:34 pmBOS-SJU
7h 04m1 stop
United Airlines Logo
1:05 am - 9:09 amSJU-BOS
8h 04m1 stop
$233United Airlines
Find Deal
Sun, Sep 21 - Mon, Sep 29
Delta Logo
5:25 am - 1:10 pmBOS-SJU
7h 45m1 stop
Delta Logo
1:27 pm - 5:39 pmSJU-BOS
4h 12mnonstop
$259Delta
Find Deal
Sat, Sep 13 - Wed, Sep 17
American Airlines Logo
5:43 am - 4:20 pmBOS-SJU
10h 37m1 stop
American Airlines Logo
3:50 pm - 12:19 amSJU-BOS
8h 29m2 stops
$263American Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
JetBlue Logo
8:00 am - 12:04 pmBOS-SJU
4h 04mnonstop
JetBlue Logo
3:15 am - 11:42 amSJU-BOS
8h 27m1 stop
$289JetBlue
Find Deal
Fri, Sep 26 - Sun, Sep 28
JetBlue Logo
12:00 pm - 4:00 pmBOS-SJU
4h 00mnonstop
JetBlue Logo
3:15 am - 9:47 amSJU-BOS
6h 32m1 stop
$311JetBlue
Find Deal
Sat, Sep 13 - Tue, Sep 16
United Airlines Logo
6:00 am - 2:43 pmBOS-SXM
8h 43m1 stop
United Airlines Logo
3:55 pm - 10:23 amSXM-BOS
18h 28m2 stops
$340United Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
Useful Info

KAYAK's insights & trends for Boston to Caribbean Islands flights

Get data-powered insights and trends into flights from Boston to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Boston to Caribbean Islands flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Boston to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Boston found in the last 72 hours was to San Juan, at $134 round-trip. The most popular route is from Boston (BOS) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $134.

Can I save money by flying with a layover from Boston to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $767, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Boston to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Caribbean Islands is September, when tickets cost $161 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $395 and $300 respectively.

What’s the cheapest day of the week to fly from Boston to Caribbean Islands?

The average price of all round-trip flights from Boston to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Boston to Caribbean Islands. For your return ticket, we recommend flying on a Friday and avoiding Tuesdays for the best deals.

How far in advance should I book a flight from Boston to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.


Good to know

Low seasonSeptember
High seasonFebruary
Cheapest flight$77
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Boston to San Juan Airport

FAQs - booking Caribbean Islands flights

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

    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 Boston to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to 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 Boston to Caribbean Islands?

    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 from Boston to Caribbean Islands with an airline and back with another airline.

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

    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 from Boston to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $280 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $299.

Top 5 airlines serving from Boston to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Boston to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Caribbean Islands? 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.
8.0
DeltaOverall score based on 7934 reviews
8.5Crew
7.9Comfort
7.3Food
7.9Entertainment
8.2Boarding
Airline reviews

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

6.0 GoodTina, Apr 2025MSP - CLT
Read more Delta reviews

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Electric plugs didn't work. Entertainment system wasn't working

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Pitch was very small. Knees were on the seat back in front of me.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

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