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Caribbean Islands

$78+ Cheap flights from Massachusetts to Caribbean Islands

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from Massachusetts to Caribbean Islands

Cheapest flights from Massachusetts to Caribbean Islands
Explore the most affordable flight options available from Massachusetts to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Sun 12/73:18 pmBDL - SJU
Nonstop3h 56mFrontier
Mon 12/158:30 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/13$195
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sun 12/76:30 pmBDL - SJU
3 stops52h 46mMultiple Airlines
Sun 12/216:00 amSJU - BDL
Nonstop4h 08mMultiple Airlines
Deal found 11/12$204
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/277:12 pmBDL - SJU
Nonstop3h 58mFrontier
Mon 12/158:30 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/11$205
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Mon 12/86:36 pmBDL - SJU
2 stops31h 14mMultiple Airlines
Fri 12/1210:45 amSJU - BDL
Nonstop4h 08mMultiple Airlines
Deal found 11/13$206
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sat 11/228:27 pmBDL - SJU
1 stop29h 27mFrontier
Wed 11/266:01 amSJU - BDL
1 stop28h 51mFrontier
Deal found 11/11$208
This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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.
Fri 12/121:19 pmBDL - SJU
1 stop12h 31mFrontier
Sun 12/216:00 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/13$210
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sat 11/2910:00 amBDL - SJU
Nonstop3h 58mFrontier
Fri 12/511:47 amSJU - BDL
2 stops48h 43mFrontier
Deal found 11/12$211
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Thu 11/208:27 pmBDL - SJU
1 stop17h 11mFrontier
Sun 11/233:12 pmSJU - BDL
Nonstop4h 05mFrontier
Deal found 11/12$212
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Tue 12/98:11 pmBOS - SJU
1 stop29h 39mMultiple Airlines
Mon 12/224:10 amSJU - BOS
1 stop7h 40mMultiple Airlines
Deal found 11/12$212
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Thu 11/202:06 pmBDL - SJU
2 stops23h 32mMultiple Airlines
Sun 11/233:12 pmSJU - BDL
Nonstop4h 05mMultiple Airlines
Deal found 11/12$213
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sun 11/235:45 amBOS - SJU
1 stop13h 42mSpirit Airlines
Wed 11/2611:55 amSJU - BOS
1 stop12h 58mSpirit Airlines
Deal found 11/12$213
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Mon 11/241:30 pmBDL - SJU
2 stops12h 24mMultiple Airlines
Thu 11/273:12 pmSJU - BDL
Nonstop4h 05mMultiple Airlines
Deal found 11/12$214

Cheap flight deals from Massachusetts to Caribbean Islands

Keep the following information in mind while searching for Massachusetts to Caribbean Islands flight deals. Data was last updated November 13, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$194
(Kiwi.com)

One-way from

$78
(Super.com)

Popular in

December

Cheapest in

January

Average price

$317
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 Islands
Search Deals
One-way flight from Massachusetts to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Caribbean Islands 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 13, 2025.
Use the filters below to find and compare flights from Massachusetts to Caribbean Islands that are best for you.

Fly from

Massachusetts

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 1/27

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Mon 2/2

2:59 pm-6:20 pm

Nonstop4h 21m

$234

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 12/24

9:15 am-2:17 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 12/31

7:45 pm-10:57 pm

Nonstop4h 12m

$238

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 12/25

9:15 am-2:17 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Mon 12/29

12:40 pm-3:53 pm

Nonstop4h 13m

$250

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 12/26

7:10 am-12:12 pm

Nonstop4h 02m

Saint Thomas Island Cyril E King

Thu 1/1

1:07 pm-5:55 pm

1 stop5h 48m

$250

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/2

7:10 am-12:12 pm

Nonstop4h 02m

Saint Thomas Island Cyril E King

Sun 1/11

2:00 pm-6:59 pm

1 stop5h 59m

$254

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 1/3

9:40 am-2:40 pm

Nonstop4h 00m

Saint Thomas Island Cyril E King

Thu 1/8

2:00 pm-6:59 pm

1 stop5h 59m

$254

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

Sun 1/25

2:00 pm-6:59 pm

1 stop5h 59m

$254

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 1/11

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 1/16

2:00 pm-6:59 pm

1 stop5h 59m

$254

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 12/8

8:10 am-1:10 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 12/11

2:20 pm-5:45 pm

Nonstop4h 25m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 12/9

8:10 am-1:10 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Tue 12/23

2:08 pm-5:36 pm

Nonstop4h 28m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $88). Flying from Massachusetts to Caribbean Islands 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 EPX?

Find hourly flight availability from Massachusetts to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

It’s typically best to fly out from Massachusetts to Caribbean Islands in the evening. Doing so could potentially save you 20% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Caribbean Islands 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.

Weekly flight availability from Massachusetts to Caribbean Islands

Explore weekly flight availability from Massachusetts to Caribbean Islands. 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 November 13, 2025.

The most flights from USMA to zzEPX are scheduled on a Thursday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Caribbean Islands. 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 Islands?

    There are many flights that can get you from Massachusetts to Caribbean Islands in 4h 02m. Fly via Delta, JetBlue, or United Airlines to get the fastest option. The distance between Massachusetts and Caribbean Islands is about 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 Islands one-way?

    The cheapest airlines for a one-way flight from Massachusetts to Caribbean Islands are Delta ($80), Spirit Airlines ($119), and Frontier ($123).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Caribbean Islands 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 Islands?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $88). Flying from Massachusetts to Caribbean Islands 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 Islands

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 Islands

Discover the top 10 airlines that operate flights from Massachusetts to Caribbean Islands. 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 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$397FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$99Average$526FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$385FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$141Average$630FlexibilityNo cancel feeOn-time67%
DeltaCheapest$144Average$483FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$190Average$514FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$192Average$345FlexibilityNo cancel feeOn-time70%
ArajetCheapest$230Average$423FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$591FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$593FlexibilityNo cancel feeOn-time71%

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