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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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
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 November 29, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$180
(Cheapflightsfares)

One-way from

$99
(Super.com)

Popular in

December

Cheapest in

January

Average price

$321

Good round-trip deal

$262 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
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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. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/27. 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 12/1010:56 amBOS - SJU
1 stop12h 20mSpirit Airlines
Fri 12/192:59 amSJU - BOS
1 stop8h 02mSpirit Airlines
Deal found 11/27$181
This CheapOair deal was found by Cheapflights users on 11/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/811:08 amBOS - SJU
1 stop12h 08mSpirit Airlines
Thu 12/184:10 amSJU - BOS
1 stop7h 40mSpirit Airlines
Deal found 11/27$182
This Kiwi.com deal was found by Cheapflights users on 11/28. 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.
Sun 12/1412:57 pmBOS - SJU
3 stops34h 48mMultiple Airlines
Thu 12/188:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Deal found 11/28$183
This Super.com deal was found by Cheapflights users on 11/28. 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.
Fri 12/51:19 pmBDL - SJU
1 stop12h 31mFrontier
Fri 12/1210:45 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/28$184
This Kiwi.com deal was found by Cheapflights users on 11/28. 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 12/95:45 amBOS - SJU
2 stops18h 04mMultiple Airlines
Thu 12/188:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Deal found 11/28$184
This Cheapflightsfares deal was found by Cheapflights users on 11/27. 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.
Sat 12/1310:56 amBOS - SJU
1 stop12h 20mSpirit Airlines
Sat 12/203:15 pmSJU - BOS
Nonstop4h 24mSpirit Airlines
Deal found 11/27$185
This Cheapflightsfares deal was found by Cheapflights users on 11/28. 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 12/811:08 amBOS - SJU
1 stop12h 08mSpirit Airlines
Fri 12/1211:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 11/28$186
This Kiwi.com deal was found by Cheapflights users on 11/27. 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.
Sun 11/307:12 pmBDL - SJU
Nonstop3h 58mFrontier
Mon 12/88:30 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/27$187
This Cheapflightsfares deal was found by Cheapflights users on 11/28. 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 12/811:08 amBOS - SJU
1 stop12h 08mSpirit Airlines
Thu 12/1111:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 11/28$188
This Priceline deal was found by Cheapflights users on 11/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:11 pmBOS - SJU
1 stop13h 22mMultiple Airlines
Sat 12/1311:05 amSJU - BOS
1 stop23h 22mMultiple Airlines
Deal found 11/27$190
This Cheapflightsfares deal was found by Cheapflights users on 11/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:04 pmBDL - SJU
1 stop29h 46mFrontier
Sun 1/113:55 amSJU - BDL
1 stop16h 29mFrontier
Deal found 11/26$192
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:56 amBOS - SJU
1 stop12h 20mSpirit Airlines
Fri 12/192:59 amSJU - BOS
1 stop8h 02mSpirit Airlines
Deal found 11/26$193

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 November 29, 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

Tue 1/27

8:05 am-1:11 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:25 pm-5:45 pm

Nonstop4h 20m

$186

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 1/28

9:05 am-8:58 pm

1 stop10h 53m

San Juan Luis Munoz Marin Intl

Mon 2/2

7:00 am-3:53 pm

1 stop9h 53m

$195

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 5/13

8:20 am-12:28 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

Tue 5/19

1:30 pm-5:53 pm

Nonstop4h 23m

$202

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/3

10:05 am-9:12 pm

1 stop10h 07m

San Juan Luis Munoz Marin Intl

Tue 3/10

6:15 am-5:32 pm

1 stop11h 17m

$211

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 2/5

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Mon 2/16

2:01 pm-6:54 pm

1 stop5h 53m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 1/29

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Mon 2/2

2:00 pm-6:49 pm

1 stop5h 49m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 1/18

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 1/23

2:00 pm-6:49 pm

1 stop5h 49m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/23

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sun 1/25

2:00 pm-6:49 pm

1 stop5h 49m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 1/6

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 1/14

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 12/31

7:10 am-12:12 pm

Nonstop4h 02m

Saint Thomas Island Cyril E King

Thu 1/8

2:00 pm-6:49 pm

1 stop5h 49m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/28

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 $87). Flying from Massachusetts to Caribbean in September is currently the most expensive (average of $147). 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 November 29, 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 evening, which can drop the price by up to 20% versus a flight in the afternoon.

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 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Caribbean flight should consider departing on Wednesday mornings 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 4h 05m. Massachusetts and Caribbean are separated by a distance of 1697 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 Delta, which is currently one of the cheapest options available, starting at $101. United Airlines flights start at $108 while deals on Southwest start at $126 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 $87). Flying from Massachusetts to Caribbean in September is currently the most expensive (average of $147). 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 November 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$87Average$414FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$370FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$136Average$513FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$141Average$609FlexibilityNo cancel feeOn-time67%
DeltaCheapest$148Average$475FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$180Average$272FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$194Average$495FlexibilityNo cancel feeOn-time69%
ArajetCheapest$230Average$435FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$593FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$593FlexibilityNo cancel feeOn-time71%

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