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$99+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheap flight deals from Massachusetts to Caribbean

Keep the following information in mind while searching for Massachusetts to Caribbean flight deals. Data was last updated septiembre 15, 2025.

Round-trip from

$176
(CheapOair)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$255

Good round-trip deal

$246 or less

Good one-way deal

$136 or less
From Massachusetts to Caribbean
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One-way flight from Massachusetts to Caribbean
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Massachusetts to Caribbean.
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Price to beat on a one-way flight from Massachusetts to Caribbean.
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Find 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 septiembre 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
sáb. 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
sáb. 2/75:27 pmSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 9/15$195
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
jue. 10/22:53 pmBOS - SJU
1 stop10h 01mSpirit Airlines
mar. 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/13$202
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
mié. 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
lun. 10/62:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/14$206
This eDestinos deal was found by Cheapflights users on 9/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/256:49 pmBOS - SJU
1 stop16h 15mSpirit Airlines
mar. 9/306:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/13$212
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
lun. 11/176:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
mié. 11/1912:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$213
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
sáb. 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
jue. 11/612:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$214
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
vie. 11/76:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
mié. 11/1212:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$215
This Priceline deal was found by Cheapflights users on 9/15. 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.
sáb. 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
vie. 11/712:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/15$217
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/411:13 amBOS - SJU
1 stop7h 08mSpirit Airlines
sáb. 12/66:00 amSJU - BOS
1 stop18h 25mSpirit Airlines
Deal found 9/12$218
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
sáb. 9/2712:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
sáb. 10/46:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/15$219
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sáb. 12/66:00 amBOS - SJU
1 stop9h 23mMultiple Airlines
sáb. 12/133:59 pmSJU - BOS
1 stop9h 45mMultiple Airlines
Deal found 9/14$223
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
mié. 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
mar. 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/14$226

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 septiembre 15, 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

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

mar. 10/21

6:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

mié. 10/29

4:50 pm-11:59 pm

1 stop7h 09m

$263

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 10/19

5:20 pm-9:10 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

dom. 10/26

6:01 am-10:04 am

Nonstop4h 03m

$274

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

sáb. 2/7

7:00 pm-11:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

sáb. 3/7

7:00 am-10:10 am

Nonstop4h 10m

$280

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

sáb. 11/8

4:15 pm-9:10 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

dom. 11/16

6:00 am-9:04 am

Nonstop4h 04m

$280

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

mié. 10/22

1:45 pm-10:45 pm

1 stop9h 00m

San Juan Luis Munoz Marin Intl

lun. 10/27

5:50 am-12:10 pm

1 stop6h 20m

$281

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 10/19

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

mié. 10/22

1:32 pm-5:45 pm

Nonstop4h 13m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

vie. 10/24

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

mar. 11/4

2:32 pm-5:45 pm

Nonstop4h 13m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

dom. 10/26

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

mar. 11/4

2:32 pm-5:45 pm

Nonstop4h 13m

$282

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

dom. 9/28

7:10 am-4:43 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

mié. 10/1

1:29 pm-10:29 pm

1 stop9h 00m

$282

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

mar. 10/21

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

dom. 10/26

1:32 pm-5:45 pm

Nonstop4h 13m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean (average of $254). Flying from Massachusetts to Caribbean in June is currently the most expensive (average of $339). 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 septiembre 15, 2025.

When flying from Massachusetts to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 septiembre 15, 2025.

The most flights from USMA to 0CB are scheduled on a Friday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 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 3h 50m. Massachusetts and Caribbean are separated by a distance of 1669 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $119. Southwest flights start at $119 while deals on Frontier start at $123 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, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean (average of $254). Flying from Massachusetts to Caribbean in June is currently the most expensive (average of $339). 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$81Average$380FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$377FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$136Average$570FlexibilityNo cancel feeOn-time62%
DeltaCheapest$142Average$480FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$187Average$357FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$188Average$651FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$192Average$412FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$194Average$533FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$591FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$560FlexibilityNo cancel feeOn-time71%

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