$69 Find Cheap Flights from Boston to Caribbean

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 departing on 2/23. 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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Cheap Flights from Boston to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$358
Santo Domingo
Santo Domingononstop$271
Montego Bay
Montego Bay1 stop$275
Oranjestad
Oranjestad2 stops$302
Nassau
Nassaunonstop$310
Kingston
Kingston1 stop$373
Simpson Bay
Simpson Bay2 stops$317
Providenciales
Providencialesnonstop$335
Port of Spain
Port of Spain2 stops$274
Bridgetown
Bridgetown1 stop$354
George Town
George Town1 stop$295
Willemstad
Willemstad1 stop$266
Castries
Castries2 stops$788
St. John's
St. John's1 stop$451
Puerto Plata
Puerto Plata1 stop$343
Aguadilla
Aguadilla1 stop$192
Punta Cana
Punta Cana1 stop$358
Santo Domingo
Santo Domingononstop$271
Montego Bay
Montego Bay1 stop$275
Oranjestad
Oranjestad2 stops$302
Nassau
Nassaunonstop$310
Kingston
Kingston1 stop$373
Simpson Bay
Simpson Bay2 stops$317
Providenciales
Providencialesnonstop$335
Port of Spain
Port of Spain2 stops$274
Bridgetown
Bridgetown1 stop$354
George Town
George Town1 stop$295
Willemstad
Willemstad1 stop$266
Castries
Castries2 stops$788
St. John's
St. John's1 stop$451
Puerto Plata
Puerto Plata1 stop$343
Aguadilla
Aguadilla1 stop$192

Book Cheap Boston to Caribbean 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 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

Tue, Feb 24 - Thu, Feb 26
Spirit Airlines Logo
5:27 am - 3:31 pm
BOS
-
SJU
9h 04m
1 stop
Spirit Airlines Logo
3:30 pm - 6:56 pm
SJU
-
BOS
4h 26mnonstop
$143Spirit Airlines
Mon, Feb 23 - Thu, Feb 26
Spirit Airlines Logo
5:27 am - 3:31 pm
BOS
-
SJU
9h 04m
1 stop
Spirit Airlines Logo
11:52 am - 11:59 pm
SJU
-
BOS
13h 07m
1 stop
$144Spirit Airlines
Tue, Apr 28 - Mon, May 4
American Airlines Logo
6:00 am - 4:25 pm
BOS
-
AUA
10h 25m
2 stops
American Airlines Logo
4:20 pm - 10:52 am
AUA
-
BOS
18h 32m
1 stop
$302American Airlines
Mon, Apr 13 - Thu, Apr 16
Delta Logo
6:18 am - 11:10 am
BOS
-
AUA
4h 52mnonstop
Delta Logo
12:25 pm - 5:29 pm
AUA
-
BOS
5h 04mnonstop
$303Delta
Wed, Mar 18 - Mon, Mar 23
American Airlines Logo
6:52 pm - 4:10 pm
BOS
-
AUA
21h 18m
1 stop
American Airlines Logo
5:13 pm - 10:57 am
AUA
-
BOS
17h 44m
1 stop
$304American Airlines
Tue, Mar 3 - Thu, Mar 12
JetBlue Logo
6:00 am - 3:05 pm
BOS
-
AUA
8h 05m
1 stop
JetBlue Logo
1:25 pm - 6:25 pm
AUA
-
BOS
5h 00mnonstop
$310JetBlue
Mon, Mar 2 - Fri, Mar 6
JetBlue Logo
1:43 pm - 5:20 pm
BOS
-
NAS
3h 37mnonstop
JetBlue Logo
12:00 pm - 3:23 pm
NAS
-
BOS
3h 23mnonstop
$310JetBlue
Wed, Mar 4 - Wed, Mar 11
Delta Logo
9:25 am - 1:07 pm
BOS
-
NAS
3h 42mnonstop
Delta Logo
2:40 pm - 6:08 pm
NAS
-
BOS
3h 28mnonstop
$311Delta
Thu, Mar 19 - Tue, Mar 24
United Airlines Logo
5:45 am - 12:50 pm
BOS
-
SXM
7h 05m
1 stop
United Airlines Logo
3:55 pm - 9:21 am
SXM
-
BOS
17h 26m
2 stops
$320United Airlines
Mon, Mar 2 - Mon, Mar 9
United Airlines Logo
6:00 am - 1:50 pm
BOS
-
SXM
6h 50m
1 stop
United Airlines Logo
3:55 pm - 11:57 pm
SXM
-
BOS
8h 02m
1 stop
$321United Airlines
Booking Insights

KAYAK's insights & trends for Boston to Caribbean flights

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

What is the cheapest Boston to Caribbean flight route?

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

The cheapest ticket to Caribbean from Boston found in the last 72 hours was to San Juan, at $125 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 $125.

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

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 $504, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Caribbean, 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 is March, when tickets cost $264 (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?

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

When flying from Boston to Caribbean, you should consider leaving on a Wednesday and avoid Fridays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Fridays and the most expensive ones on Mondays.

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

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, 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, you should book around 3 weeks before departure, which saves you about 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$69
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Boston to San Juan Airport

FAQs - booking Caribbean flights

  • Which destination in the Caribbean is most flown to from Boston?

    Many of the flights from Boston to the Caribbean visit San Juan because the city is close to Boston. This makes it one of the shortest flights from Boston to the Caribbean. When visiting San Juan from Boston, you don’t need a passport as a US citizen, making your travel to the Caribbean city hassle-free. San Juan is also accessible to other Caribbean islands, allowing you to explore the Caribbean easily from the airport.

  • Which airlines with flights from Boston to the Caribbean allow pets in the cabin?

    If you want to take your pet on your flight from Boston to the Caribbean, consider flying Delta Air Lines, which allows small pets up to 20 pounds to travel in the cabin from Boston to the Caribbean. Ensure your pet is in a carrier with dimensions of 18 x 11 x 11 inches.

  • Can a minor fly unaccompanied from Boston to the Caribbean?

    Consider booking Delta, United, and American Airlines, which allow kids between 5 and 14 years to travel alone for an additional fee under the unaccompanied minor service. As the parent or guardian of the child traveling alone, ensure you have the unaccompanied minor form, your identification documents, the contact details of the adult picking up the child at the destination airport, and the child’s birth certificate or passport for proof of age.

  • Does Boston Logan International Airport offer accessibility services?

    If you have special needs, BOS offers airport and wheelchair assistance and has accessible restrooms, parking, and seating to aid passengers with limited mobility. The airport has elevators and escalators for access to terminal levels by passengers with reduced mobility, braille signage for the visually impaired, visual paging, and TTY phones for hard-of-hearing passengers.

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

    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.

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

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

    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 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?

    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 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?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $290 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $332.

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from Boston to the following destinations at these prices or less: San Juan $118 one-way - $204 round-trip
  • Flights from Boston to the Caribbean depart from Boston Logan International Airport (BOS), the primary airport serving Boston and surrounding areas. The airport is a hub for Delta Air Lines and is a focus city for JetBlue Airlines. You can connect to several Caribbean destinations from BOS through these airlines, as they offer frequent flights to the Caribbean.
  • Delta Air Lines has a Delta Comfort+ class, which is between Delta's economy class and their first class. Comfort+ offers extra legroom, priority boarding, dedicated overhead bin space, and additional in-flight amenities for a comfortable flight from Boston to the Caribbean.
  • JetBlue offers a generous carry-on baggage allowance with baggage weight up to 22 lb and maximum dimensions of 22 x 14 x 9 inches for economy passengers on flights from Boston to the Caribbean. The airline also allows you to have an extra personal item, such as a laptop bag or purse, with dimensions up to 17 x 13 x 8 inches.
  • If you want to spend less time traveling from Boston to the Caribbean, book a direct flight from Boston to the Caribbean. Many airlines, including Delta, American, JetBlue, and Spirit Airlines, offer direct flights to various Caribbean destinations, including San Juan (SJU), Punta Cana (PUJ), Nassau (NAS), Montego Bay (MBJ), and Aruba (AUA).
  • Most airlines, including JetBlue, Delta, and American Airlines, offering flights from Boston to the Caribbean offer special meals upon request. You can inform the airlines of your dietary needs in advance. The airlines provide vegetarian, vegan, gluten-free, low-sodium, child, and diabetic meals.

Reviews of the top 5 airlines serving from Boston to Caribbean

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

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

10.0 ExcellentSharon, Feb 2026
TPA - ATL
Read more Delta reviews

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.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

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.

Very old flight - time to retire it for newer airplanes

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

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.

Much better than Spirit. I was please by the easy fast check in and boarding

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 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!!

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

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.

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.

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

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.

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.

They cancelled my flight last minute, forcing me to rebook with another airline.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports