$88 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 4/29. 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$380
Santo Domingo
Santo Domingo1 stop$273
Montego Bay
Montego Bay1 stop$328
Oranjestad
Oranjestad1 stop$300
Nassau
Nassaunonstop$320
Kingston
Kingston1 stop$410
Simpson Bay
Simpson Bay1 stop$316
Providenciales
Providencialesnonstop$356
Port of Spain
Port of Spain1 stop$320
Bridgetown
Bridgetown1 stop$304
George Town
George Town1 stop$314
Willemstad
Willemstad2 stops$312
Castries
Castries2 stops$681
Puerto Plata
Puerto Plata1 stop$325
St. John's
St. John's1 stop$432
Aguadilla
Aguadilla1 stop$212
Punta Cana
Punta Cana1 stop$380
Santo Domingo
Santo Domingo1 stop$273
Montego Bay
Montego Bay1 stop$328
Oranjestad
Oranjestad1 stop$300
Nassau
Nassaunonstop$320
Kingston
Kingston1 stop$410
Simpson Bay
Simpson Bay1 stop$316
Providenciales
Providencialesnonstop$356
Port of Spain
Port of Spain1 stop$320
Bridgetown
Bridgetown1 stop$304
George Town
George Town1 stop$314
Willemstad
Willemstad2 stops$312
Castries
Castries2 stops$681
Puerto Plata
Puerto Plata1 stop$325
St. John's
St. John's1 stop$432
Aguadilla
Aguadilla1 stop$212

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

Wed, Apr 29 - Wed, May 6
Frontier Logo
11:16 am - 2:01 am
BOS
-
SJU
14h 45m
1 stop
Frontier Logo
3:33 pm - 9:12 am
SJU
-
BOS
17h 39m
1 stop
$168Frontier
Tue, May 5 - Fri, May 8
Frontier Logo
6:00 am - 2:07 pm
BOS
-
SJU
8h 07m
1 stop
Frontier Logo
5:15 pm - 1:24 am
SJU
-
BOS
8h 09m
1 stop
$174Frontier
Tue, Apr 14 - Thu, Apr 16
Spirit Airlines Logo
3:23 pm - 7:19 pm
BOS
-
SJU
3h 56mnonstop
Spirit Airlines Logo
7:00 am - 7:06 pm
SJU
-
BOS
12h 06m
1 stop
$177Spirit Airlines
Tue, Apr 14 - Mon, Apr 20
Spirit Airlines Logo
3:23 pm - 7:19 pm
BOS
-
SJU
3h 56mnonstop
Spirit Airlines Logo
2:59 am - 10:29 am
SJU
-
BOS
7h 30m
1 stop
$184Spirit Airlines
Mon, Apr 13 - Thu, Apr 16
Delta Logo
8:45 am - 12:42 pm
BOS
-
STT
3h 57mnonstop
Delta Logo
2:33 pm - 6:59 pm
STT
-
BOS
4h 26mnonstop
$201Delta
Tue, Apr 14 - Wed, Apr 15
Delta Logo
6:00 am - 1:13 pm
BOS
-
STT
7h 13m
1 stop
Delta Logo
2:33 pm - 6:59 pm
STT
-
BOS
4h 26mnonstop
$206Delta
Wed, May 6 - Tue, May 12
American Airlines Logo
8:45 am - 4:15 pm
BOS
-
STT
7h 30m
1 stop
American Airlines Logo
5:05 pm - 10:02 am
STT
-
BOS
16h 57m
1 stop
$215American Airlines
Sat, May 2 - Thu, May 7
American Airlines Logo
6:00 am - 1:09 pm
BOS
-
UVF
7h 09m
1 stop
American Airlines Logo
3:28 pm - 10:01 am
UVF
-
BOS
18h 33m
1 stop
$300American Airlines
Sat, May 2 - Sat, May 9
JetBlue Logo
7:00 am - 10:23 am
BOS
-
NAS
3h 23mnonstop
JetBlue Logo
11:39 am - 2:59 pm
NAS
-
BOS
3h 20mnonstop
$320JetBlue
Sat, May 30 - Sat, Jun 6
JetBlue Logo
7:00 am - 10:23 am
BOS
-
NAS
3h 23mnonstop
JetBlue Logo
11:23 am - 2:40 pm
NAS
-
BOS
3h 17mnonstop
$345JetBlue
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 $142 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 $142.

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

The average price for all round-trip flights from Boston to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $284 on average. Morning departures are around 25% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $354.

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 $578, 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 January, when tickets cost $267 (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 $364 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 Thursdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Thursdays 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 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$89
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 22% 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.

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 $140 one-way - $269 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 8374 reviews
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
7.9Comfort
Airline reviews

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

6.0 GoodJoseph, Apr 2026
MSP - RIC
Read more Delta reviews

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

The wheelchair service is useless. They live you in different spots, not tell you anything just wait. I waited 30 minutes in Frankfurt when decided to walk the 25 minutes distance. In Budapest nobody came.

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

Fine. The issues I had were associated with luggage being delayed from Turkey to Tanzania

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

Flight was on-time, boarding was flawless and the crew was friendly.

The staff are very, very professional. It's what flying should feel like.

Horrible airline .. my flight was cancel , the only offer to flight next day was no good for me , representative from spirit advise everybody to buy the new ticket from southwest airline and spirit will pay back the money we spend on new ticket but after we did this they don’t want to pay us back , .. customer service is not help anybody Chat text messages it is horrible also , robots can’t answer and help u with anything … I send the complains to head quarter in Miami and department of transportation

Attention to detail. Luggage was lost in flight, after I confirmed it was connecting. Never made it to the destination airport.

The ticket price are reasonable, however, they can do better with the price on the luggage. Overall, I will continue using spirit.

That this is my second time the they cancel flights and they always wait until the last minute to let people know

The flight was supposed to leave at 6:22pm we are just now leaving the gate after deplaning twice at 1:07am.

Spirit is always late. Every single time. Always a different reason

They keep delaying and cancel at last moment and height was for you to get refund need to be in chat line for two hours. I complained to DOT. Never recommend this airline on Kayak please

First flight in along time with spirit! I’m honored to say this flight was excellent 😊

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Every connection was late but that meant I was not running from one to the next so that was a good thing. No one wants to miss a connection

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports