$92 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 7/19. 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.
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Best Caribbean Flight Deals from Boston

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$257
Santo Domingo
Santo Domingo1 stop$258
Montego Bay
Montego Bay1 stop$274
Oranjestad
Oranjestad1 stop$347
Nassau
Nassaunonstop$350
Kingston
Kingston1 stop$302
Simpson Bay
Simpson Bay1 stop$331
Providenciales
Providenciales1 stop$339
Port of Spain
Port of Spain2 stops$437
Bridgetown
Bridgetownnonstop$391
George Town
George Townnonstop$315
Willemstad
Willemstad2 stops$364
Castries
Castries2 stops$851
St. John's
St. John's1 stop$369
Puerto Plata
Puerto Plata1 stop$367
Aguadilla
Aguadilla1 stop$264
Punta Cana
Punta Cana1 stop$257
Santo Domingo
Santo Domingo1 stop$258
Montego Bay
Montego Bay1 stop$274
Oranjestad
Oranjestad1 stop$347
Nassau
Nassaunonstop$350
Kingston
Kingston1 stop$302
Simpson Bay
Simpson Bay1 stop$331
Providenciales
Providenciales1 stop$339
Port of Spain
Port of Spain2 stops$437
Bridgetown
Bridgetownnonstop$391
George Town
George Townnonstop$315
Willemstad
Willemstad2 stops$364
Castries
Castries2 stops$851
St. John's
St. John's1 stop$369
Puerto Plata
Puerto Plata1 stop$367
Aguadilla
Aguadilla1 stop$264

Cheap Flights from Boston to Caribbean

 
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

Sun, Aug 3 - Wed, Aug 6
Spirit Airlines Logo
6:10 am - 9:09 pmBOS-SJU
14h 59m1 stop
Spirit Airlines Logo
3:50 pm - 11:48 pmSJU-BOS
7h 58m1 stop
$169Spirit Airlines
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Sat, Aug 2 - Thu, Aug 7
Spirit Airlines Logo
7:26 pm - 12:02 pmBOS-SJU
16h 36m1 stop
Spirit Airlines Logo
3:13 pm - 7:30 pmSJU-BOS
4h 17mnonstop
$174Spirit Airlines
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Sat, Nov 1 - Sat, Nov 8
JetBlue Logo
9:25 am - 1:24 pmBOS-STT
3h 59mnonstop
JetBlue Logo
2:30 pm - 7:31 pmSTT-BOS
6h 01m1 stop
$302JetBlue
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Thu, Oct 2 - Mon, Oct 6
American Airlines Logo
6:00 am - 4:00 pmBOS-STT
10h 00m2 stops
American Airlines Logo
5:15 pm - 7:55 amSTT-BOS
14h 40m2 stops
$311American Airlines
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Fri, Sep 5 - Mon, Sep 8
JetBlue Logo
7:00 am - 11:05 amBOS-PUJ
4h 05mnonstop
JetBlue Logo
12:30 pm - 4:39 pmPUJ-BOS
4h 09mnonstop
$330JetBlue
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Fri, Sep 19 - Fri, Sep 26
Delta Logo
5:35 am - 1:50 pmBOS-SXM
8h 15m1 stop
Delta Logo
3:20 pm - 1:18 amSXM-BOS
9h 58m1 stop
$335Delta
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Fri, Aug 15 - Sat, Aug 30
United Airlines Logo
6:05 am - 12:29 pmBOS-SXM
6h 24m1 stop
United Airlines Logo
3:55 pm - 12:36 pmSXM-BOS
20h 41m2 stops
$340United Airlines
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Fri, Aug 15 - Sat, Aug 30
United Airlines Logo
6:05 am - 12:29 pmBOS-SXM
6h 24m1 stop
United Airlines Logo
3:55 pm - 10:35 amSXM-BOS
18h 40m1 stop
$342United Airlines
Find Deal
Mon, Nov 10 - Tue, Nov 25
Delta Logo
6:00 am - 2:35 pmBOS-SXM
7h 35m1 stop
Delta Logo
4:00 pm - 1:00 amSXM-BOS
10h 00m1 stop
$345Delta
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Sat, Aug 23 - Sat, Aug 30
American Airlines Logo
6:00 am - 1:27 pmBOS-NAS
7h 27m2 stops
American Airlines Logo
12:44 pm - 6:17 pmNAS-BOS
5h 33m1 stop
$356American Airlines
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Boston to Caribbean.

The cheapest ticket to Caribbean from Boston found in the last 72 hours was to San Juan, at $202 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 $202.

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 $1,101, 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 $161 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $393 and $309 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 Saturdays 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 Tuesdays.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.


Good to know

Low seasonSeptember
High seasonFebruary
Cheapest flight$92
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 6% 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 morning, when round-trip flights cost $290 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $333.

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.
8.0
DeltaOverall score based on 7951 reviews
7.9Comfort
8.5Crew
7.3Food
8.2Boarding
7.9Entertainment
Airline reviews

Everything was fine except the entertainment was not working for half of the flight.

8.0 ExcellentEileen, Jul 2025BOS - PBI
Read more Delta reviews

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Great. Very smooth. Plenty of information. However, wish they would give out a menu in advance of making a dinner choice like other international airlines. The flight attendant says chicken or pasta and there are details about ingredients or spices requiring the passenger to ask which requires the flight attendant to answer many times. So easy to solve this problem. P

I'm a tall guy and even the seats with more leg room were not as comfortable as I had hoped.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

Flight was delayed again and again ultimately almost three hours getting us to our location at close to midnight by the time we got in and out of airport to destination. I had taken time off work to enjoy an evening at destination and that was now wasted

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

The flight delay in Dallas created a domino effect that impacted all of the connecting flights. It also increased the number of connections. I missed my flight from Casablanca to Marrakech because of the tight turnaround when landing in Casablanca. . CMN airport was understaffed. Only one person could help while other employees were just watching him. It was an extremely frustrating situation. People were crying and slamming their palms on the counter when speaking to the customer service provider, Allabough (man’s name?). Allabough couldn’t change my flight in the system. simultaneously, I was on the call with America. Airlines customer service rep named Solomon that said he couldn’t change it either. So, I took a ONYA voyages train to from Casablanca to Marrakech to get there on Friday June 26. This was unpredictable trip.

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

It was okay delay was long but I made it

Flight was cancelled. No reason given. No apologies. Next available flight is two days later. Ruined our 4th of July plans.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

Flight delayed over 3 or 4 hours because no captain to fly plane. I couldn’t make a connection and had to wait 9 hours for another flight. Had to fly red eye flight. Sucks

it was a quick trip. seats aren't that comfortable but because it was a quick trip it was ok. You need to have an N/A in your rating as I didn't have any food or entertainment so the only thing I could do was score low.

We paid for upgrade seats (3A & 3B) the seats on front and the seats behind us got complimentary water & soda, but we got charged, had to pay for everything. Does not make any sense ?

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

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