$113 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 8/4. 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 Cananonstop$398
Santo Domingo
Santo Domingononstop$319
Montego Bay
Montego Baynonstop$388
Oranjestad
Oranjestadnonstop$368
Nassau
Nassaunonstop$366
Kingston
Kingston1 stop$396
Simpson Bay
Simpson Bay1 stop$327
Providenciales
Providenciales1 stop$395
Port of Spain
Port of Spain1 stop$346
Bridgetown
Bridgetown1 stop$354
George Town
George Town1 stop$313
Willemstad
Willemstad2 stops$346
Castries
Castries2 stops$912
Aguadilla
Aguadilla1 stop$312
Puerto Plata
Puerto Plata1 stop$450
St. John's
St. John's1 stop$567
Punta Cana
Punta Cananonstop$398
Santo Domingo
Santo Domingononstop$319
Montego Bay
Montego Baynonstop$388
Oranjestad
Oranjestadnonstop$368
Nassau
Nassaunonstop$366
Kingston
Kingston1 stop$396
Simpson Bay
Simpson Bay1 stop$327
Providenciales
Providenciales1 stop$395
Port of Spain
Port of Spain1 stop$346
Bridgetown
Bridgetown1 stop$354
George Town
George Town1 stop$313
Willemstad
Willemstad2 stops$346
Castries
Castries2 stops$912
Aguadilla
Aguadilla1 stop$312
Puerto Plata
Puerto Plata1 stop$450
St. John's
St. John's1 stop$567

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, Sep 5 - Sat, Sep 12
United Airlines Logo
5:45 am - 12:58 pm
BOS
-
STT
7h 13m
1 stop
United Airlines Logo
2:10 pm - 1:14 am
STT
-
BOS
11h 04m
2 stops
$255United Airlines
Sat, Jun 6 - Fri, Jun 12
JetBlue Logo
6:10 pm - 10:12 pm
BOS
-
SJU
4h 02mnonstop
JetBlue Logo
5:54 pm - 10:01 pm
SJU
-
BOS
4h 07mnonstop
$274JetBlue
Sun, Aug 23 - Thu, Aug 27
Frontier Logo
6:00 am - 2:15 pm
BOS
-
SJU
8h 15m
1 stop
Frontier Logo
5:15 pm - 1:27 am
SJU
-
BOS
8h 12m
1 stop
$280Frontier
Mon, Aug 24 - Thu, Aug 27
Frontier Logo
6:00 am - 2:15 pm
BOS
-
SJU
8h 15m
1 stop
Frontier Logo
5:15 pm - 1:27 am
SJU
-
BOS
8h 12m
1 stop
$284Frontier
Sun, Sep 6 - Fri, Sep 11
Arajet Logo
10:20 pm - 2:35 am
BOS
-
SDQ
4h 15mnonstop
Arajet Logo
6:30 am - 10:45 am
SDQ
-
BOS
4h 15mnonstop
$320Arajet
Sun, Jun 7 - Sun, Jun 14
Arajet Logo
10:20 pm - 2:35 am
BOS
-
SDQ
4h 15mnonstop
Arajet Logo
4:35 pm - 8:50 pm
SDQ
-
BOS
4h 15mnonstop
$323Arajet
Sat, Aug 15 - Wed, Aug 26
Delta Logo
7:20 pm - 1:53 pm
BOS
-
SXM
18h 33m
1 stop
Delta Logo
3:18 pm - 1:25 am
SXM
-
BOS
10h 07m
1 stop
$327Delta
Sat, Aug 22 - Sat, Sep 5
American Airlines Logo
6:00 am - 3:52 pm
BOS
-
STT
9h 52m
2 stops
American Airlines Logo
2:00 pm - 9:43 pm
STT
-
BOS
7h 43m
1 stop
$335American Airlines
Sat, Jun 13 - Sat, Jun 20
Delta Logo
6:06 am - 2:15 pm
BOS
-
SXM
8h 09m
1 stop
Delta Logo
3:40 pm - 7:24 am
SXM
-
BOS
15h 44m
1 stop
$362Delta
Mon, Aug 24 - Fri, Aug 28
American Airlines Logo
7:45 am - 3:14 pm
BOS
-
PUJ
7h 29m
1 stop
American Airlines Logo
4:14 pm - 11:41 pm
PUJ
-
BOS
7h 27m
1 stop
$407American 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 7 days was to Santo Domingo, at $185 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 7 days was $296.

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 $286 on average. Morning departures are around 30% 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 $372.

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 $611, 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 September, when tickets cost $410 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $582 and $531 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 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 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$113
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Boston to Saint Thomas Island

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

  • 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 8445 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.8Comfort
8.5Crew
Airline reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

10.0 Excellentangela, May 2026
LGA - PBI
Read more Delta reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

This flight is a quick way to get to Chicago, but a bit expensive.

Very comfortable seating and the Flight staff were very attentive. The premium economy section that I was seated in was very clean, updated, and well appointed. I would highly recommend flying United Airlines as this experience was better than the Japan Airlines business class that I flew several months ago.

Our flight was canceled same day and we were never informed. Had to pay more and worse seating on another airline.

Our flight to Rome, Italy was cancelled the day of and we were never informed. We only found out because I was trying to get into my husbands account and called to get his account number. Had to pay more for worse seating on another airline.

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

First class ticket gets you no seat back entertainment? I have to bring my own laptop to see a movie? And most of their movies have ADS? No thank you. Worse: Tiny snacks only on a 2 hr flight?

Late- that’s what United does best. Missed my connection, rebooked to a flight 17 hours later and had to spend $500 on a hotel. What did I get? A $15 meal voucher. What can you get in an airport for $15. I hate United so much.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

THEY WENT OUT OF BUSINESS AND CANCELED FLIGHT. REPLACEMENT FLIGHTS WERE 300% HIGHER SO MY FAMILY COULD NOT GET TOGETHER. WHY AM I GETTING THIS SURVEY?????

If there WAS a flight it would have been EXCELENT..Maybe?

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

There was no flight. Spirit went bankrupt Right before my departure and kayak did not refund me any money. I would like my refund kayak. How can I get it? Please let me know. Thank you

Flights were canceled due to airline shutting down and haven’t received a reimbursement. Had to book last minute new flights which were expensive

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Are you serious? I know this is an automated message but how can you not update the system?

Had a flight change had to get a credit.will I get my money back.

Shut down without prior notice End up with spending lots of extra $$$

There was a crack in my window seal. And Spirit is now closed forever.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports