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Caribbean

$77+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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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 December 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Fri 1/1610:52 amSJU - BOS
Nonstop4h 20mSpirit Airlines
Deal found 12/27$194
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Sat 1/2410:52 amSJU - BOS
Nonstop4h 20mSpirit Airlines
Deal found 12/27$207
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sat 1/246:11 pmSJU - BOS
1 stop8h 02mMultiple Airlines
Deal found 12/27$215
This Expedia deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Fri 1/93:55 amSJU - BOS
1 stop8h 13mMultiple Airlines
Deal found 12/27$217
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Fri 1/163:58 amSJU - BOS
1 stop8h 12mMultiple Airlines
Deal found 12/27$219
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Thu 1/156:00 amSJU - BOS
1 stop9h 38mSpirit Airlines
Deal found 12/27$229
This Cheapflightsfares deal was found by Cheapflights users on 12/25. 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.
Wed 12/3110:03 amBDL - SJU
Nonstop3h 56mFrontier
Thu 1/84:07 pmSJU - BDL
1 stop28h 32mFrontier
Deal found 12/25$233
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Fri 1/910:52 amSJU - BOS
Nonstop4h 20mSpirit Airlines
Deal found 12/27$238
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Sat 1/1710:52 amSJU - BOS
Nonstop4h 20mSpirit Airlines
Deal found 12/27$241
This Frontier deal was found by Cheapflights users on 12/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:03 amBDL - SJU
Nonstop3h 56mFrontier
Fri 1/98:20 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 12/26$244
This Priceline deal was found by Cheapflights users on 12/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:01 amBOS - SJU
Nonstop3h 59mMultiple Airlines
Sat 1/3110:52 amSJU - BOS
Nonstop4h 20mMultiple Airlines
Deal found 12/26$245
This Kiwi.com deal was found by Cheapflights users on 12/27. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sat 1/103:55 amSJU - BOS
1 stop7h 16mMultiple Airlines
Deal found 12/27$252

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 December 28, 2025.

Round-trip from

$148
(Kiwi.com)

One-way from

$77
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$386

Good round-trip deal

$221 or less

Good one-way deal

$99 or less
From Massachusetts to Caribbean
Search Deals
One-way flight from Massachusetts to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($25 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 December 2025
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 December 28, 2025.
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

Sun 2/8

10:30 am-10:22 pm

2 stops10h 52m

San Juan Luis Munoz Marin Intl

Fri 2/13

5:50 pm-11:57 pm

1 stop7h 07m

$197

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/24

9:30 am-10:22 pm

2 stops11h 52m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-9:14 am

1 stop8h 09m

$197

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 3/22

7:20 pm-11:23 pm

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Thu 3/26

5:10 am-9:22 am

Nonstop4h 12m

$202

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/2

8:20 am-12:28 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

Sat 5/9

1:30 pm-5:53 pm

Nonstop4h 23m

$202

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 4/25

5:59 pm-10:01 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Sat 5/2

5:01 am-9:12 am

Nonstop4h 11m

$202

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 2/16

5:01 am-10:02 am

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Sat 2/21

12:10 pm-3:24 pm

Nonstop4h 14m

$202

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/10

8:05 am-1:11 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Thu 2/19

7:00 am-3:15 pm

1 stop9h 15m

$207

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/10

6:55 am-5:17 pm

1 stop9h 22m

San Juan Luis Munoz Marin Intl

Tue 2/17

7:00 am-3:15 pm

1 stop9h 15m

$211

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/2

3:28 pm-11:50 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Fri 5/8

1:00 am-7:49 am

1 stop6h 49m

$211

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 3/26

6:00 am-12:07 pm

1 stop6h 07m

San Juan Luis Munoz Marin Intl

Mon 3/30

1:17 pm-10:54 pm

1 stop9h 37m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

Showing 1-10 of 60 results
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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 $88). 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 December 28, 2025.

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 24% 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 December 27, 2025.

Travelers seeking maximum savings on their Massachusetts to Caribbean flight should consider departing on Sunday at noon 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.

Weekly flight availability from Massachusetts to Caribbean

Explore weekly flight availability from Massachusetts to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 28, 2025.

The most flights from USMA to 0CB are scheduled on a Friday (19 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (10 on average).

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 4h 03m. 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 $59 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 $88). 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.
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Top 10 airlines flying from Massachusetts to Caribbean

Discover the top 10 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$417FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$98Average$366FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$99Average$498FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$141Average$605FlexibilityNo cancel feeOn-time67%
DeltaCheapest$151Average$471FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$179Average$397FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$190Average$491FlexibilityNo cancel feeOn-time69%
ArajetCheapest$206Average$438FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$234Average$597FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$684FlexibilityNo cancel feeOn-time71%

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