$71 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 1/31. 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

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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Flight Deals

Cheap Flights from Boston to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$346
Santo Domingo
Santo Domingononstop$349
Montego Bay
Montego Baynonstop$347
Oranjestad
Oranjestad1 stop$284
Nassau
Nassau1 stop$315
Kingston
Kingston1 stop$443
Simpson Bay
Simpson Baynonstop$339
Providenciales
Providenciales1 stop$341
Port of Spain
Port of Spain1 stop$262
Bridgetown
Bridgetown1 stop$355
George Town
George Town1 stop$247
Willemstad
Willemstad1 stop$286
Castries
Castries3 stops$1,826
St. John's
St. John's1 stop$385
Puerto Plata
Puerto Plata2 stops$324
Aguadilla
Aguadilla1 stop$211
Punta Cana
Punta Cananonstop$346
Santo Domingo
Santo Domingononstop$349
Montego Bay
Montego Baynonstop$347
Oranjestad
Oranjestad1 stop$284
Nassau
Nassau1 stop$315
Kingston
Kingston1 stop$443
Simpson Bay
Simpson Baynonstop$339
Providenciales
Providenciales1 stop$341
Port of Spain
Port of Spain1 stop$262
Bridgetown
Bridgetown1 stop$355
George Town
George Town1 stop$247
Willemstad
Willemstad1 stop$286
Castries
Castries3 stops$1,826
St. John's
St. John's1 stop$385
Puerto Plata
Puerto Plata2 stops$324
Aguadilla
Aguadilla1 stop$211

Book Cheap Boston to Caribbean Islands Plane Tickets

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Caribbean Islands

Tue, Jan 6 - Sat, Jan 24
Multiple Airlines Logo
12:31 pm - 5:30 pm
BOS
-
SJU
3h 59mnonstop
Multiple Airlines Logo
10:52 am - 2:12 pm
SJU
-
BOS
4h 20mnonstop
$149Multiple Airlines
Sat, Feb 7 - Fri, Feb 13
Multiple Airlines Logo
7:00 am - 11:33 pm
BOS
-
SJU
15h 33m1 stop
Multiple Airlines Logo
6:00 am - 9:19 am
SJU
-
BOS
4h 19mnonstop
$150Multiple Airlines
Tue, Mar 17 - Sun, Mar 22
JetBlue Logo
9:45 am - 1:46 pm
BOS
-
STT
4h 01mnonstop
JetBlue Logo
2:41 pm - 8:34 pm
STT
-
BOS
5h 53m1 stop
$218JetBlue
Tue, Jan 27 - Mon, Feb 2
Delta Logo
8:55 am - 2:00 pm
BOS
-
STT
4h 05mnonstop
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
$224Delta
Sat, Jan 17 - Sat, Jan 31
JetBlue Logo
11:55 am - 4:54 pm
BOS
-
STT
3h 59mnonstop
JetBlue Logo
5:50 pm - 10:38 pm
STT
-
BOS
5h 48m1 stop
$225JetBlue
Fri, Feb 6 - Mon, Feb 9
Delta Logo
6:00 am - 1:22 pm
BOS
-
STT
6h 22m1 stop
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
$229Delta
Sat, Jan 10 - Thu, Jan 29
United Airlines Logo
7:22 pm - 1:45 pm
BOS
-
GCM
18h 23m2 stops
United Airlines Logo
2:25 pm - 9:52 pm
GCM
-
BOS
7h 27m1 stop
$270United Airlines
Tue, Mar 3 - Tue, Mar 10
United Airlines Logo
6:00 am - 1:15 pm
BOS
-
GCM
7h 15m1 stop
United Airlines Logo
4:45 pm - 12:49 pm
GCM
-
BOS
19h 04m2 stops
$275United Airlines
Sat, Jan 10 - Wed, Jan 14
American Airlines Logo
6:41 am - 1:22 pm
BOS
-
NAS
6h 41m1 stop
American Airlines Logo
2:00 pm - 8:11 pm
NAS
-
BOS
6h 11m1 stop
$317American Airlines
Fri, Jan 9 - Mon, Jan 12
American Airlines Logo
6:00 am - 1:22 pm
BOS
-
NAS
7h 22m2 stops
American Airlines Logo
12:09 pm - 8:11 pm
NAS
-
BOS
8h 02m1 stop
$319American Airlines
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Boston found in the last 72 hours was to San Juan, at $114 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 $114.

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 $427, 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 January, when tickets cost $242 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $386 and $361 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 Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Boston to Caribbean Islands. For your return ticket, we recommend flying on a Saturday and avoiding Mondays 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 2 weeks before departure, which saves you about 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$71
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Boston to George Town

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 $313 on average. Morning departures are around 3% 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 $338.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Boston to the following destinations at these prices or less: San Juan $122 one-way - $238 round-trip

Reviews of the 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.
7.9
DeltaOverall score based on 8010 reviews
7.3Food
7.9Comfort
7.9Entertainment
8.1Boarding
8.5Crew
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

United have really come back. Airport and boarding process is clear and good, app and information also very good

They charged a fee for 1st bag checked. Others in same party were free.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Not comparable to Qatar Airways services on flights to Doha. Flight attendants provided basic services; I was never recognized by name or as an Executive Platinum member. Restrooms were not kept clean during the flight.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

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.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

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.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

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).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Our flight got rescheduled 48 hours later, the airline didn’t pay a penny for our expenses.

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Flight was in time, very smooth ride and surprisingly lots of legroom in the cabin so I certainly will fly with spirit again

The seats are the most uncomfortable seats I’ve ever sat in. Don’t believe I’ll ever fly spirit again!!

Flight was canceled and instead of rescheduling at the gate we had to go out to the ticket counter. Unruly kids kicking the back of my rows chair with staff to inattentive to say something.

Customer feedback I sent to Spirited today: “I will never fly Spirit Airlines again and will work hard to convince my friends and family to boycott/avoid Spirit Airlines at all costs. I booked three seats for me and my 8 and 10 year old children on NK 1222 from Orlando to Kansas City for 12/7/25 leaving Orlando at 10:37AM. This itinerary was abandoned by Spirit and we were rebooked onto Spirit flight NK 213 leaving at 9:06PM without any notice. Then the nightmare really began. Flight 213 was delayed a total of 12 times, finally leaving at 6:35AM the following day. The gate was changed 5 times and our electronic boarding passes were invalidated at midnight. The worst part was that the 12 separate delays were incremental making it impossible to plan for accommodations for my family. My kids missed a day of school and barely slept under the harsh lights with lots of noise on the filthy airport floor. The customer service agent at Spirit Airlines told us we would be emailed a voucher for a hotel which never happened. I asked about it multiple times and it never arrived in my email inbox. This whole unfortunate situation could’ve been avoided if spirit had taken a realistic approach and delayed the flight from 9 PM until 6 AM from the beginning. My son gleefully deleted the Spirit app from my phone once we landed and we will never fly with Spirit again.”

Honestly horrible. The plane on the way back was delayed 6 times with no explanation on why. When I asked for a refund or some money back because I had to miss a day of work because of the desk, they told me no. Because of how poorly it was handled I will most likely never take spirit again

I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta

30 minute delay, Also there was a medical emergency on the flight. The flight crew was on top of the situation and assisted the medical professionals that happened to be on the flight.

This was my first time on a budget airline and I couldn't even sit down all the way because my knees would embed in the seat in front of me. I'm only 6' tall with a 32" inseam. There's no upside other than y'all are cheap. I'm glad it was only a 2 hour flight. Lesson learned! I get why everybody talks down on budget airlines. The staff was outstanding, the flight went as well as possible, great pilot, great boarding, smooth sailing. Zero chance I'll be back though.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports