$82 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 12/7. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$338
Santo Domingo
Santo Domingo2 stops$377
Montego Bay
Montego Bay2 stops$364
Oranjestad
Oranjestad2 stops$369
Nassau
Nassau1 stop$343
Kingston
Kingston1 stop$433
Simpson Bay
Simpson Bay2 stops$372
Providenciales
Providencialesnonstop$350
Port of Spain
Port of Spain1 stop$420
Bridgetown
Bridgetown1 stop$279
George Town
George Town1 stop$268
Willemstad
Willemstad1 stop$314
Castries
Castries3 stops$823
St. John's
St. John's1 stop$409
Puerto Plata
Puerto Plata1 stop$286
Aguadilla
Aguadilla2 stops$271
Punta Cana
Punta Cana1 stop$338
Santo Domingo
Santo Domingo2 stops$377
Montego Bay
Montego Bay2 stops$364
Oranjestad
Oranjestad2 stops$369
Nassau
Nassau1 stop$343
Kingston
Kingston1 stop$433
Simpson Bay
Simpson Bay2 stops$372
Providenciales
Providencialesnonstop$350
Port of Spain
Port of Spain1 stop$420
Bridgetown
Bridgetown1 stop$279
George Town
George Town1 stop$268
Willemstad
Willemstad1 stop$314
Castries
Castries3 stops$823
St. John's
St. John's1 stop$409
Puerto Plata
Puerto Plata1 stop$286
Aguadilla
Aguadilla2 stops$271

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

Sat, Feb 21 - Thu, Feb 26
Frontier Logo
10:24 am - 3:28 pmBOS-SJU
4h 04mnonstop
Frontier Logo
6:00 am - 9:23 amSJU-BOS
4h 23mnonstop
$214Frontier
Find Deal
Sat, Jan 24 - Tue, Jan 27
Spirit Airlines Logo
9:39 pm - 9:52 amBOS-SJU
11h 13m1 stop
Spirit Airlines Logo
12:10 pm - 10:08 pmSJU-BOS
10h 58m1 stop
$216Spirit Airlines
Find Deal
Tue, Dec 9 - Sat, Dec 13
JetBlue Logo
12:55 pm - 5:57 pmBOS-SJU
4h 02mnonstop
JetBlue Logo
6:45 am - 9:58 amSJU-BOS
4h 13mnonstop
$223JetBlue
Find Deal
Sat, Jan 24 - Wed, Feb 4
JetBlue Logo
1:00 pm - 6:02 pmBOS-SJU
4h 02mnonstop
JetBlue Logo
6:15 am - 9:25 amSJU-BOS
4h 10mnonstop
$262JetBlue
Find Deal
Sat, Nov 29 - Fri, Dec 5
American Airlines Logo
5:40 am - 4:30 pmBOS-STT
9h 50m1 stop
American Airlines Logo
6:17 pm - 12:59 amSTT-BOS
7h 42m1 stop
$285American Airlines
Find Deal
Sun, Dec 14 - Fri, Dec 19
United Airlines Logo
5:30 am - 1:56 pmBOS-STT
7h 26m1 stop
United Airlines Logo
5:20 pm - 11:54 pmSTT-BOS
7h 34m1 stop
$293United Airlines
Find Deal
Mon, Nov 17 - Fri, Nov 21
American Airlines Logo
6:00 am - 2:16 pmBOS-STT
7h 16m1 stop
American Airlines Logo
4:27 pm - 10:56 pmSTT-BOS
7h 29m1 stop
$295American Airlines
Find Deal
Mon, Feb 2 - Wed, Feb 11
Delta Logo
8:55 am - 2:00 pmBOS-STT
4h 05mnonstop
Delta Logo
2:59 pm - 6:20 pmSTT-BOS
4h 21mnonstop
$302Delta
Find Deal
Mon, Jan 19 - Mon, Jan 26
Delta Logo
8:55 am - 2:00 pmBOS-STT
4h 05mnonstop
Delta Logo
4:15 pm - 1:04 amSTT-BOS
9h 49m1 stop
$307Delta
Find Deal
Sun, Nov 16 - Sun, Nov 23
United Airlines Logo
6:00 am - 4:18 pmBOS-STT
9h 18m1 stop
United Airlines Logo
3:05 pm - 12:45 amSTT-BOS
10h 40m1 stop
$332United Airlines
Find Deal
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 Montego Bay, at $167 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 $175.

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 $536, 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 $223 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $375 and $345 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 Monday and avoid Fridays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Saturdays 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 2 weeks before departure, which saves you about 13% 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$82
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from Boston to Simpson Bay

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 morning, when round-trip flights cost $313 on average. Morning departures are around 2% cheaper 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 $348.

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 $166 one-way - $262 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 8004 reviews
8.5Crew
7.9Comfort
8.2Boarding
7.9Entertainment
7.3Food
Airline reviews

I truly love flying with Delta. They have always treated me with the upmost respect

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

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

They have the most inexperienced / rude flight staff I’ve encountered

The Hawaiian lady that boarded me was rude and the one help me a the ticket counter was rude

My experience was terrible. They cancelled my flight twice. They kept delaying it and leading me on, acting like the flight was going to go when it never had a chance. I missed out on valuable family time because of spirit and I won’t be flying with them again.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

The flight was cancelled at the last minute. Will never fly Spirit again. Without a doubt the worst airline around.

My flight was delayed several times and eventually cancelled. Then the re-booked flight for 8pm was delayed multiple times over, and eventually it would have forced me to be at the airport for 9 hours. I accepted a rebook for the following day, fortunately I was able to stay with my friend again in New York, but if I didn’t have him as a resource it would have been much more upsetting.

Horrible, delay after delay due to our plane needing fuel.

Rough landings but comfortable and affordable if you can pack light

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.