$69 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 $[0,preposition:'from ']$[0,article:'from ']$[0,place:'from'] $[1,preposition:'to ']$[1,article:'to ']$[1,place:'to'] departing on 2/21. 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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1 adult, Economy, 0 bags

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Cheap Flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to']

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$349
Santo Domingo
Santo Domingo1 stop$284
Montego Bay
Montego Bay1 stop$267
Oranjestad
Oranjestad1 stop$327
Nassau
Nassaunonstop$301
Kingston
Kingston1 stop$362
Simpson Bay
Simpson Bay1 stop$316
Providenciales
Providenciales1 stop$335
Port of Spain
Port of Spain1 stop$269
Bridgetown
Bridgetown1 stop$350
George Town
George Town1 stop$260
Willemstad
Willemstad1 stop$270
Castries
Castries2 stops$799
St. John's
St. John's1 stop$456
Puerto Plata
Puerto Plata1 stop$341
Aguadilla
Aguadilla1 stop$202
Punta Cana
Punta Cana1 stop$349
Santo Domingo
Santo Domingo1 stop$284
Montego Bay
Montego Bay1 stop$267
Oranjestad
Oranjestad1 stop$327
Nassau
Nassaunonstop$301
Kingston
Kingston1 stop$362
Simpson Bay
Simpson Bay1 stop$316
Providenciales
Providenciales1 stop$335
Port of Spain
Port of Spain1 stop$269
Bridgetown
Bridgetown1 stop$350
George Town
George Town1 stop$260
Willemstad
Willemstad1 stop$270
Castries
Castries2 stops$799
St. John's
St. John's1 stop$456
Puerto Plata
Puerto Plata1 stop$341
Aguadilla
Aguadilla1 stop$202

Book Cheap $[0, place:'genitive'] $[1, preposition:'to ']$[1,article:'to ']$[1, place:'to'] Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights $[0,preposition:'from ']$[0,article:'from ']$[0,place:'from'] $[1, preposition:'to ']$[1,article:'to ']$[1, place:'to'] 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 $[0,preposition:'from ']$[0,article:'from ']$[0,place:'from'] $[1,preposition:'to '] $[1,article:'to ']$[1,place:'to']

Mon, Feb 23 - Thu, Feb 26
Spirit Airlines Logo
3:00 pm - 8:06 pm
BOS
-
SJU
4h 06mnonstop
Spirit Airlines Logo
11:52 am - 11:59 pm
SJU
-
BOS
13h 07m
1 stop
$144Spirit Airlines
Mon, Mar 2 - Fri, Mar 6
Spirit Airlines Logo
8:01 pm - 1:08 am
BOS
-
SJU
4h 07mnonstop
Spirit Airlines Logo
11:52 am - 11:59 pm
SJU
-
BOS
13h 07m
1 stop
$145Spirit Airlines
Wed, Mar 4 - Wed, Mar 11
Delta Logo
9:25 am - 1:07 pm
BOS
-
NAS
3h 42mnonstop
Delta Logo
2:40 pm - 6:08 pm
NAS
-
BOS
3h 28mnonstop
$301Delta
Fri, Feb 20 - Thu, Feb 26
Delta Logo
6:00 am - 11:50 am
BOS
-
NAS
5h 50m
1 stop
Delta Logo
6:27 pm - 10:01 am
NAS
-
BOS
15h 34m
1 stop
$305Delta
Mon, Feb 23 - Wed, Mar 4
American Airlines Logo
9:25 am - 3:36 pm
BOS
-
NAS
6h 11m
1 stop
American Airlines Logo
1:57 pm - 8:21 pm
NAS
-
BOS
6h 24m
1 stop
$307American Airlines
Fri, Feb 27 - Fri, Mar 6
American Airlines Logo
5:49 am - 11:40 am
BOS
-
NAS
5h 51m
1 stop
American Airlines Logo
12:11 pm - 11:59 pm
NAS
-
BOS
11h 48m
1 stop
$315American Airlines
Fri, Mar 20 - Wed, Mar 25
United Airlines Logo
5:45 am - 12:50 pm
BOS
-
SXM
7h 05m
1 stop
United Airlines Logo
3:55 pm - 11:10 am
SXM
-
BOS
19h 15m
2 stops
$317United Airlines
Thu, Mar 5 - Thu, Mar 12
JetBlue Logo
7:54 am - 1:10 pm
BOS
-
SXM
4h 16mnonstop
JetBlue Logo
1:25 pm - 6:00 pm
SXM
-
BOS
4h 35mnonstop
$319JetBlue
Mon, Apr 13 - Tue, Apr 21
JetBlue Logo
6:00 am - 10:07 am
BOS
-
SXM
4h 07mnonstop
JetBlue Logo
11:45 am - 4:12 pm
SXM
-
BOS
4h 27mnonstop
$320JetBlue
Thu, Mar 5 - Mon, Mar 9
United Airlines Logo
6:00 am - 3:22 pm
BOS
-
NAS
9h 22m
1 stop
United Airlines Logo
1:05 pm - 9:41 pm
NAS
-
BOS
8h 36m
2 stops
$320United Airlines
Booking Insights

KAYAK's insights & trends for $[0,place:'default'] $[1,preposition:'to ']$[1,article:'to ']$[1,place:'to'] flights

Get data-powered insights and trends into flights $[0,preposition:'from ']$[0,article:'from ']$[0,place:'from'] $[1,preposition:'to ']$[1,article:'to ']$[1,place:'to'] 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 $126 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 $126.

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 $508, 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 $253 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $386 and $359 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 Sundays 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 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$69
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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 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 to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from 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 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 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 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 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 evening, when round-trip flights cost $290 on average. Morning departures are around 13% more expensive 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 $334.

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from to the following destinations at these prices or less: San Juan $102 one-way - $203 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 $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from ']$[1, preposition:'to ']$[1, article:'to ']$[1, place:'to']

 
Need help choosing which airline to fly with $[0,preposition:'from ']$[0,article:'from ']$[0,place:'from'] $[1,preposition:'to ']$[1,article:'to ']$[1,place:'to']? 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 8162 reviews
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
7.9Comfort
Airline reviews

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

6.0 GoodCindy, Feb 2026
SMF - GDL
Read more Delta reviews

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

did not have enough meal for first class passengers so offer us snack

Arrived 40 min early which was great - sat in runway for 35 min so no gain. Then waited for luggage 45 min. They need to staff accordingly knowing its one of the busiest week in Phx

Broke my luggage and I can't get a resolution yet.

My flight got rerouted due to crew rest. I was sent to Dallas customer service was not very polite. Was given a $40 room voucher for Motel 6 and $12 to eat with. It delayed me by a day. Where if I would have just stuck with my original flight Arizona was delayed to Cleveland and I could have made it home. They put me on a 9:00 flight out of Dallas to Cleveland without my knowledge or consent. When originally I was told it would be 8:45 a.m. on February 1st. I told them I could not take the 9:00 flight because I did not have anybody to pick me up from the airport at that time. I'm extremely disappointed in how I was treated. And I will not fly American Airlines again.

I am very appreciative of the help provided to me by Dennis and Whitney. I had lost my phone at EWR airport and they were very kind in assisting me. This included advice on how to file a report and also helping me connect with family. The pilot was also great about keeping passengers updated on the flight progress with regular communications over the system.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

Old equipment, needs upgrade and seat comfort. Internet didn't work 75% or the time.

The screens were inoperable for movies and such, but everything else was just fine

For a 5 1/2 hour flite i considered the "business class" to be subpar. The seats were just ok, no amenities, really nothing more than a long domestic flight. Frankly disappointed.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Cancelled my flight, said next flight was 30hrs later. Had to come out of pocket $500 to get on a SW flight

All of our flights were canceled, though every other airline was flying out and in

We were on the tarmac waiting for a gate at Logan for 40, minutes. The crew handled it well. Can't blame the airline.

That gate is like a ducking shelter at Newark No where to sit Outlets that don’t work Bathrooms that are dirty

Everything was good. On time, boarding fast, flight attendants friendly.

Great, but seats are terrible. Way too cramped for any human.

Spirit has always and will always stink. Absolute worst airline around.

It was smooth sailing snags we had a really smooth landing and a great flight!

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports