$84 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 2/2. 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$348
Santo Domingo
Santo Domingo1 stop$369
Montego Bay
Montego Bay1 stop$355
Oranjestad
Oranjestad1 stop$313
Nassau
Nassau1 stop$313
Kingston
Kingston1 stop$395
Simpson Bay
Simpson Baynonstop$339
Providenciales
Providenciales2 stops$344
Port of Spain
Port of Spain1 stop$235
Bridgetown
Bridgetown1 stop$330
George Town
George Town1 stop$251
Willemstad
Willemstad1 stop$246
Castries
Castries2 stops$754
St. John's
St. John's1 stop$409
Puerto Plata
Puerto Plata1 stop$298
Aguadilla
Aguadilla1 stop$202
Punta Cana
Punta Cana1 stop$348
Santo Domingo
Santo Domingo1 stop$369
Montego Bay
Montego Bay1 stop$355
Oranjestad
Oranjestad1 stop$313
Nassau
Nassau1 stop$313
Kingston
Kingston1 stop$395
Simpson Bay
Simpson Baynonstop$339
Providenciales
Providenciales2 stops$344
Port of Spain
Port of Spain1 stop$235
Bridgetown
Bridgetown1 stop$330
George Town
George Town1 stop$251
Willemstad
Willemstad1 stop$246
Castries
Castries2 stops$754
St. John's
St. John's1 stop$409
Puerto Plata
Puerto Plata1 stop$298
Aguadilla
Aguadilla1 stop$202

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, Dec 30 - Wed, Jan 14
Multiple Airlines Logo
7:34 pm - 12:41 am
BOS
-
SJU
4h 07mnonstop
Multiple Airlines Logo
4:35 pm - 1:13 am
SJU
-
BOS
9h 38m1 stop
$160Multiple Airlines
Sat, Jan 24 - Mon, Feb 9
Spirit Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
Spirit Airlines Logo
10:52 am - 2:12 pm
SJU
-
BOS
4h 20mnonstop
$161Spirit Airlines
Tue, Feb 3 - Fri, Feb 6
JetBlue Logo
8:00 am - 1:05 pm
BOS
-
STT
4h 05mnonstop
JetBlue Logo
2:00 pm - 6:59 pm
STT
-
BOS
5h 59m1 stop
$234JetBlue
Thu, Jan 29 - Tue, Feb 3
JetBlue Logo
8:00 am - 1:05 pm
BOS
-
STT
4h 05mnonstop
JetBlue Logo
2:00 pm - 6:49 pm
STT
-
BOS
5h 49m1 stop
$235JetBlue
Mon, Jan 19 - Mon, Jan 26
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
$239Delta
Tue, Jan 13 - Wed, Jan 21
Delta Logo
6:00 am - 1:22 pm
BOS
-
STT
6h 22m1 stop
Delta Logo
3:10 pm - 10:32 pm
STT
-
BOS
8h 22m1 stop
$243Delta
Mon, Jan 19 - Fri, Jan 23
American Airlines Logo
6:05 am - 1:46 pm
BOS
-
STT
6h 41m1 stop
American Airlines Logo
4:47 pm - 11:05 pm
STT
-
BOS
7h 18m1 stop
$244American Airlines
Sat, Jan 31 - Sat, Feb 7
Frontier Logo
6:00 am - 5:09 pm
BOS
-
NAS
11h 09m1 stop
Frontier Logo
6:29 pm - 1:13 am
NAS
-
BOS
6h 44m1 stop
$313Frontier
Tue, Dec 16 - Sun, Dec 21
American Airlines Logo
8:00 am - 5:55 pm
BOS
-
NAS
9h 55m2 stops
American Airlines Logo
2:00 pm - 9:54 pm
NAS
-
BOS
7h 54m1 stop
$334American Airlines
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
6:00 am - 3:38 pm
BOS
-
PLS
9h 38m1 stop
Frontier Logo
4:50 pm - 1:13 am
PLS
-
BOS
8h 23m1 stop
$355Frontier
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 $170 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 $170.

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 $517, 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 $224 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $379 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 Wednesday 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 11% 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$84
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 23% 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 $318 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 $343.

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 $141 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 8010 reviews
7.9Comfort
8.5Crew
7.9Entertainment
7.3Food
8.1Boarding
Airline reviews

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

10.0 ExcellentCharles, Dec 2025
DTW - PHX
Read more Delta reviews

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.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

My flight was delayed about three hours. I got home at 3:30 in the morning very bad experience.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

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

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Terrible Airline I will never fly that airline again. Shame on you for recommending them.

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

I didn't eat, so I can't rate the food. Delayed set off was beyond

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

I hope you continue to be one of the great company

Crew are always very angry and dismissive like they seem they are being forced to work. In addition, there was a long line for the bathrooms, and only one was allowed to be used. No reason was given for only one bathroom being available; apparently, the stewardess was more interested in using the jumpseat instead of allowing the customers to use the bathroom.

Very positive in both directions. Safe travels, nice staff, lost and found in fact found my phone under my chair! I was out of cash after my NYC trip otherwise I would've offered a reward for helping my day out immensly! Thanks you so much Spirit staff!

I stopped flying spirit as much because they are crooks and thieves. It's not like other airlines where you can at least get credits they just take your money.

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports