$94 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 2/8. 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 from Boston to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$351
Santo Domingo
Santo Domingo2 stops$373
Montego Bay
Montego Bay1 stop$362
Oranjestad
Oranjestadnonstop$373
Nassau
Nassau1 stop$345
Kingston
Kingston1 stop$432
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providencialesnonstop$340
Port of Spain
Port of Spain1 stop$420
Bridgetown
Bridgetown1 stop$303
George Town
George Town1 stop$271
Willemstad
Willemstad1 stop$307
Castries
Castries2 stops$719
St. John's
St. John's1 stop$415
Puerto Plata
Puerto Plata1 stop$304
Aguadilla
Aguadilla1 stop$332
Punta Cana
Punta Cana1 stop$351
Santo Domingo
Santo Domingo2 stops$373
Montego Bay
Montego Bay1 stop$362
Oranjestad
Oranjestadnonstop$373
Nassau
Nassau1 stop$345
Kingston
Kingston1 stop$432
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providencialesnonstop$340
Port of Spain
Port of Spain1 stop$420
Bridgetown
Bridgetown1 stop$303
George Town
George Town1 stop$271
Willemstad
Willemstad1 stop$307
Castries
Castries2 stops$719
St. John's
St. John's1 stop$415
Puerto Plata
Puerto Plata1 stop$304
Aguadilla
Aguadilla1 stop$332

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

Sun, Nov 16 - Fri, Nov 21
Multiple Airlines Logo
6:16 am - 5:19 pmBOS-SJU
10h 03m1 stop
Multiple Airlines Logo
2:25 am - 7:29 amSJU-BOS
30h 04m1 stop
$214Multiple Airlines
Find Deal
Wed, Jan 14 - Wed, Jan 21
Spirit Airlines Logo
6:15 am - 7:21 pmBOS-SJU
12h 06m1 stop
Spirit Airlines Logo
12:10 pm - 10:08 pmSJU-BOS
10h 58m1 stop
$216Spirit Airlines
Find Deal
Thu, Jan 1 - Thu, Jan 8
Frontier Logo
12:18 pm - 5:22 pmBOS-SJU
4h 04mnonstop
Frontier Logo
8:25 am - 11:48 amSJU-BOS
4h 23mnonstop
$218Frontier
Find Deal
Sun, Nov 16 - Mon, Nov 24
Frontier Logo
8:40 am - 1:32 amBOS-SJU
15h 52m2 stops
Frontier Logo
3:59 am - 10:04 amSJU-BOS
7h 05m1 stop
$220Frontier
Find Deal
Tue, Dec 2 - Fri, Dec 5
JetBlue Logo
6:55 pm - 11:54 pmBOS-SJU
3h 59mnonstop
JetBlue Logo
1:41 pm - 4:54 pmSJU-BOS
4h 13mnonstop
$223JetBlue
Find Deal
Tue, Dec 2 - Fri, Dec 12
JetBlue Logo
6:55 pm - 11:54 pmBOS-SJU
3h 59mnonstop
JetBlue Logo
11:34 am - 7:56 pmSJU-BOS
9h 22m1 stop
$240JetBlue
Find Deal
Wed, Nov 5 - Wed, Nov 12
Delta Logo
8:15 am - 1:21 pmBOS-SJU
4h 06mnonstop
Delta Logo
3:20 pm - 11:55 pmSJU-BOS
9h 35m1 stop
$267Delta
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Wed, Jan 14 - Wed, Jan 21
Delta Logo
8:55 am - 2:00 pmBOS-STT
4h 05mnonstop
Delta Logo
2:59 pm - 6:20 pmSTT-BOS
4h 21mnonstop
$302Delta
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Sat, Dec 13 - Sun, Dec 21
American Airlines Logo
5:21 am - 4:51 pmBOS-STT
10h 30m1 stop
American Airlines Logo
6:36 pm - 12:59 amSTT-BOS
7h 23m1 stop
$303American Airlines
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Sat, Jan 17 - Thu, Jan 22
American Airlines Logo
6:23 pm - 1:10 pmBOS-STT
17h 47m1 stop
American Airlines Logo
1:50 pm - 10:56 pmSTT-BOS
10h 06m2 stops
$311American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Boston to Caribbean flights

Get data-powered insights and trends into flights from Boston to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Boston to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Boston found in the last 72 hours was to Montego Bay, at $167 round-trip. The most popular route is from Boston (BOS) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $174.

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 $543, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Boston to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Caribbean is January, when tickets cost $223 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $380 and $345 respectively.

What’s the cheapest day of the week to fly from Boston to Caribbean?

The average price of all round-trip flights from Boston to Caribbean clicked on KAYAK for each day over the last 12 months.

When flying from Boston to Caribbean, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

How far in advance should I book a flight from Boston to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Caribbean, you should book around 2 weeks before departure, which saves you about 13% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 29% 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 $314 on average. Morning departures are around 3% 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 $349.

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 $165 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 7992 reviews
7.3Food
8.2Boarding
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

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

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

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

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

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

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

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

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

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

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

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

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

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

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

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

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

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

very difficult boarding process - aggressive passengers not the friendliest crew

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

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

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

The gate agents for spirit at EWR wouldn’t give me my ticket to board when I arrived 50 min from the flight, saying that I wouldn’t make my flight. They tried to reschedule me to arrive at my destination 14 hours after the original flight, which included a 10 hr layover in another city. I rebooked with another airline and it took me a total of 5 min to go through security. Then I see a charge on my card for a $100 change fee that I did not approve. Beware of this horrible place and these horrible people

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

Waited at the airport for over 4 hours to board this flight. Terrible airline

Was supposed to take off 8:00 last night. Got delayed till 8:00 this morning

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

When the flight ticket is expensive and you have to purchase check in luggage and there is no snacks, no entertainment, tight seats stuffed in the back of the plane not such good experience. I would like some to reach out to me . I paid for check luggage when I bought the ticket they made me pay again on the return flight extra $70. Very frustrating.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

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

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

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

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

i was unable to check in the flight. refund requested

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

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

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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