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$104+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Nov 25 — Dec 21
Tue 11/25
Tue 12/2
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 October 26, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$214
(Priceline)

One-way from

$104
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$264

Good round-trip deal

$274 or less

Good one-way deal

$143 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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High demand for flights, 0% potential price rise
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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 October 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 October 26, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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.
Mon 12/811:08 amBOS - SJU
1 stop12h 08mSpirit Airlines
Fri 12/1211:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 10/26$216
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/164:10 pmBDL - SJU
Nonstop3h 55mJetBlue
Wed 11/196:01 amSJU - BDL
Nonstop4h 03mJetBlue
Deal found 10/25$218
This Frontier deal was found by Cheapflights users on 10/24. 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.
Fri 12/52:48 pmBDL - SJU
Nonstop3h 56mFrontier
Thu 12/113:55 amSJU - BDL
1 stop9h 29mFrontier
Deal found 10/24$219
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/17:43 pmBOS - SJU
Nonstop4h 00mJetBlue
Fri 11/78:10 pmSJU - BOS
Nonstop4h 06mJetBlue
Deal found 10/25$219
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/306:00 amBOS - SJU
2 stops42h 06mMultiple Airlines
Wed 1/73:15 pmSJU - BOS
Nonstop4h 24mMultiple Airlines
Deal found 10/26$220
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 1/85:27 pmSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 10/23$221
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 12/3010:37 amBOS - SJU
2 stops37h 29mMultiple Airlines
Thu 1/85:27 pmSJU - BOS
Nonstop4h 07mMultiple Airlines
Deal found 10/23$222
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/187:40 amBOS - SJU
Nonstop4h 04mJetBlue
Fri 11/219:25 pmSJU - BOS
Nonstop4h 05mJetBlue
Deal found 10/25$223
This Trip.com deal was found by Cheapflights users on 10/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/181:55 pmBOS - SJU
Nonstop4h 02mJetBlue
Tue 11/259:25 pmSJU - BOS
Nonstop4h 05mJetBlue
Deal found 10/25$225
This Kiwi.com deal was found by Cheapflights users on 10/24. 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 12/3111:09 amBOS - SJU
1 stop11h 45mMultiple Airlines
Wed 1/73:15 pmSJU - BOS
Nonstop4h 24mMultiple Airlines
Deal found 10/24$226
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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.
Thu 11/136:16 amBOS - SJU
1 stop10h 03mSpirit Airlines
Thu 11/207:20 amSJU - BOS
1 stop10h 30mSpirit Airlines
Deal found 10/26$227
This Cheapflightsfares deal was found by Cheapflights users on 10/24. 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.
Thu 11/207:12 pmBDL - SJU
Nonstop3h 58mFrontier
Thu 11/273:12 pmSJU - BDL
Nonstop4h 05mFrontier
Deal found 10/24$229

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 October 26, 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 12/7

6:55 pm-11:54 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Sat 12/13

6:10 am-9:19 am

Nonstop4h 09m

$260

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 10/31

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 11/4

2:32 pm-5:45 pm

Nonstop4h 13m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 12/19

9:15 am-2:17 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Sat 12/27

8:35 pm-11:47 pm

Nonstop4h 12m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 11/16

6:55 pm-11:54 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Tue 11/25

9:25 pm-12:30 am

Nonstop4h 05m

$262

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 10/31

2:00 pm-9:50 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Mon 11/3

5:45 am-11:30 am

1 stop6h 45m

$263

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Tue 11/11

6:10 am-9:26 pm

2 stops14h 16m

San Juan Luis Munoz Marin Intl

Tue 11/18

2:05 am-2:11 pm

2 stops13h 06m

$263

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 11/5

8:15 am-1:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Wed 11/19

3:20 pm-11:54 pm

1 stop9h 34m

$263

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 11/10

4:24 pm-12:36 am

1 stop7h 12m

San Juan Luis Munoz Marin Intl

Sat 11/15

7:45 am-5:43 pm

1 stop10h 58m

$271

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/24

12:45 pm-12:36 am

2 stops10h 51m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-9:14 am

1 stop8h 09m

$271

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 11/10

12:25 pm-12:36 am

2 stops11h 11m

San Juan Luis Munoz Marin Intl

Thu 11/13

2:05 am-7:34 am

1 stop6h 29m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/24

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 $84). 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 October 26, 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 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 Delta, which is currently one of the cheapest options available, starting at $104. Southwest flights start at $132 while deals on United Airlines start at $134 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 $84). 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

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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 October 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$397FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$101Average$388FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$136Average$542FlexibilityNo cancel feeOn-time62%
DeltaCheapest$144Average$482FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$188Average$630FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$190Average$519FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$192Average$387FlexibilityNo cancel feeOn-time70%
ArajetCheapest$216Average$413FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$593FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$593FlexibilityNo cancel feeOn-time71%

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