HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$69+ Cheap flights from Massachusetts to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Massachusetts to Caribbean

Cheapest flights from Massachusetts to Caribbean
Explore the most affordable flight options available from Massachusetts to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:27 am
BOS
-
SJU
1 stop9h 04m
Spirit Airlines
Fri 2/2711:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/9$143
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:27 am
BOS
-
SJU
1 stop9h 04m
Spirit Airlines
Thu 2/2611:52 am
SJU
-
BOS
1 stop13h 07m
Spirit Airlines
Deal found 2/10$144
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Fri 2/2711:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/10$145
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:01 pm
BOS
-
SJU
Nonstop4h 07m
Multiple Airlines
Thu 3/56:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/9$146
This Expedia deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:00 pm
BOS
-
SJU
Nonstop4h 06m
Multiple Airlines
Fri 2/276:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/12$147
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/244:22 pm
BOS
-
SJU
1 stop16h 55m
Multiple Airlines
Thu 2/266:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/10$149
This Orbitz deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Wed 3/1110:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/12$151
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:18 am
BOS
-
SJU
Nonstop3h 59m
Multiple Airlines
Tue 4/1410:00 am
SJU
-
BOS
Nonstop4h 18m
Multiple Airlines
Deal found 2/10$152
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:27 am
BOS
-
SJU
1 stop9h 04m
Spirit Airlines
Sun 3/111:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/9$153
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:04 am
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Thu 3/511:52 am
SJU
-
BOS
1 stop13h 07m
Multiple Airlines
Deal found 2/11$154
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:55 pm
BDL
-
SJU
Nonstop3h 51m
Frontier
Wed 2/255:25 pm
SJU
-
BDL
1 stop18h 12m
Frontier
Deal found 2/10$186
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:49 am
BDL
-
SJU
1 stop13h 54m
Frontier
Tue 3/246:00 am
SJU
-
BDL
Nonstop4h 15m
Frontier
Deal found 2/10$187

Find flight deals from Massachusetts to Caribbean

Keep the following information in mind while searching for Massachusetts to Caribbean flight deals. Data was last updated February 12, 2026.

Round-trip from

$143
(Cheapflightsfares)

One-way from

$69
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$299

Good round-trip deal

$204 or less

Good one-way deal

$118 or less
From Massachusetts to Caribbean
Search Deals
One-way flight from Massachusetts to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Massachusetts to Caribbean.
Search Deals
Price to beat on a one-way flight from Massachusetts to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
Use the filters below to find and compare flights from Massachusetts to Caribbean that are best for you.

Fly from

Massachusetts

Fly to

Caribbean

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 3/2

4:22 pm-10:17 am

1 stop16h 55m

San Juan Luis Munoz Marin Intl

Thu 3/5

11:52 am-11:59 pm

1 stop13h 07m

$182

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 5/12

7:00 am-2:32 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Tue 5/19

3:43 pm-11:18 pm

1 stop7h 35m

$188

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 3/30

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Thu 4/2

2:45 pm-7:04 pm

Nonstop4h 19m

$231

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 4/14

10:40 pm-2:39 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Mon 4/20

11:25 pm-3:25 am

Nonstop4h 00m

$233

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 3/9

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Thu 3/12

2:45 pm-7:04 pm

Nonstop4h 19m

$241

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 4/20

10:05 am-9:24 pm

2 stops11h 19m

San Juan Luis Munoz Marin Intl

Wed 4/22

1:00 am-7:53 am

1 stop6h 53m

$242

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 3/16

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Wed 3/25

3:55 pm-10:54 pm

1 stop6h 59m

$246

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 3/4

6:55 am-4:22 pm

1 stop8h 27m

Saint Thomas Island Cyril E King

Wed 3/11

2:45 pm-7:04 pm

Nonstop4h 19m

$246

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 5/12

5:40 am-1:19 pm

1 stop7h 39m

San Juan Luis Munoz Marin Intl

Tue 5/19

1:30 pm-5:53 pm

Nonstop4h 23m

$248

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 3/11

6:00 am-1:00 pm

1 stop7h 00m

Saint Thomas Island Cyril E King

Wed 3/18

12:49 pm-8:49 pm

1 stop8h 00m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Massachusetts to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Caribbean

What is the cheapest month to book a flight from Massachusetts to Caribbean?

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Caribbean (average of $93). Flying from Massachusetts to Caribbean in November is currently the most expensive (average of $177). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to CB?

Find hourly flight availability from Massachusetts to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.

When flying from Massachusetts to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 23% versus a flight at noon.

What is the cheapest day to fly from Massachusetts to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Caribbean. Price data was last updated on February 7, 2026.

Travelers seeking maximum savings on their Massachusetts to Caribbean flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Massachusetts to Caribbean?

    Departing from Massachusetts to Caribbean will take you 3h 59m. Massachusetts and Caribbean are separated by a distance of 1678 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Massachusetts to Caribbean one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $44. Delta flights start at $54 while deals on Spirit Airlines start at $61 one-way.

  • Can I find deals for flights from Massachusetts to Caribbean that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Caribbean.

  • Can I find deals for business class flights from Massachusetts to Caribbean?

    Yes. Cheapflights offers flight deals from Massachusetts to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Caribbean?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Caribbean (average of $93). Flying from Massachusetts to Caribbean in November is currently the most expensive (average of $177). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
San Francisco to John F Kennedy Intl flights
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Miami flights
San Francisco to Newark flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
Newark to West Palm Beach flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Cancún flights
San Francisco to LaGuardia flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Cancún flights
John F Kennedy Intl to Las Vegas flights
Newark to Las Vegas flights
Newark to Orlando flights
Newark to Luis Munoz Marin Intl flights
Los Angeles to John F Kennedy Intl flights
Los Angeles to Haneda flights
O'Hare Intl to Sky Harbor Intl flights
John F Kennedy Intl to Mexico City flights
Newark to Tampa flights
O'Hare Intl to Dallas/Fort Worth flights
Seattle to Los Angeles flights
Seattle to Las Vegas flights
O'Hare Intl to Cancún flights
Dallas/Fort Worth to John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
Boston to Fort Lauderdale flights
John F Kennedy Intl to Tampa flights
Baltimore to Fort Lauderdale flights
Los Angeles to Seattle flights
LaGuardia to Tampa flights
LaGuardia to Orlando flights
Dulles Intl to Miami flights
LaGuardia to Dallas/Fort Worth flights
Boston to Miami flights
John F Kennedy Intl to Dallas/Fort Worth flights
Los Angeles to Narita flights
John F Kennedy Intl to Heathrow flights
Baltimore to Miami flights
Minneapolis to Sky Harbor Intl flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to LaGuardia flights
San Francisco to Las Vegas flights
Newark to Dallas/Fort Worth flights
Dallas/Fort Worth to Las Vegas flights

Top 9 airlines flying from Massachusetts to Caribbean

Discover the top 9 airlines that operate flights from Massachusetts to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$400FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$347FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$130Average$614FlexibilityNo cancel feeOn-time67%
DeltaCheapest$137Average$447FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$141Average$496FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$166Average$471FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$179Average$366FlexibilityNo cancel feeOn-time70%
ArajetCheapest$187Average$380FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$234Average$579FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.