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$78+ Cheap flights from Caribbean Islands to Massachusetts

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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Dec 14 — Dec 211
Sun 12/14
Sun 12/21
1 adult, Economy
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Find flight deals from Caribbean Islands to Massachusetts

Cheapest flights from Caribbean Islands to Massachusetts
Explore the most affordable flight options available from Caribbean Islands to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 14, 2025.

This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:07 pmSTT - BOS
1 stop5h 48mJetBlue
Tue 12/307:10 amBOS - STT
Nonstop4h 02mJetBlue
Deal found 11/12$229
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:01 amSJU - BOS
1 stop19h 43mFrontier
Sat 11/296:00 amBOS - SJU
1 stop18h 06mFrontier
Deal found 11/12$231
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/229:49 amSJU - BOS
2 stops16h 30mFrontier
Thu 1/16:00 amBOS - SJU
1 stop17h 37mFrontier
Deal found 11/12$232
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 12/138:00 amSJU - BOS
2 stops16h 56mMultiple Airlines
Sun 1/47:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Deal found 11/11$233
This Delta deal was found by Cheapflights users on 11/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:48 pmSTT - BOS
1 stop8h 20mDelta
Tue 12/308:20 amBOS - STT
Nonstop4h 04mDelta
Deal found 11/10$234
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.
Fri 12/124:10 amSJU - BOS
2 stops30h 17mMultiple Airlines
Mon 1/511:55 amBOS - SJU
1 stop9h 10mMultiple Airlines
Deal found 11/11$234
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.
Thu 11/2011:55 amSJU - BOS
1 stop12h 58mSpirit Airlines
Mon 11/245:45 pmBOS - SJU
1 stop16h 04mSpirit Airlines
Deal found 11/13$235
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2211:55 amSJU - BOS
1 stop12h 58mSpirit Airlines
Sat 11/295:45 amBOS - SJU
1 stop13h 42mSpirit Airlines
Deal found 11/13$236
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 11/207:11 amSJU - BOS
2 stops42h 33mMultiple Airlines
Sun 11/235:45 pmBOS - SJU
1 stop16h 04mMultiple Airlines
Deal found 11/12$237
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:01 amSJU - BDL
1 stop28h 51mFrontier
Sat 11/2910:00 amBDL - SJU
Nonstop3h 58mFrontier
Deal found 11/12$238
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:30 pmSTT - BOS
1 stop11h 03mAmerican Airlines
Tue 12/305:59 amBOS - STT
1 stop7h 00mAmerican Airlines
Deal found 11/12$238
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.
Tue 12/163:55 amSJU - BOS
1 stop30h 57mMultiple Airlines
Fri 1/95:28 amBOS - SJU
1 stop17h 24mMultiple Airlines
Deal found 11/13$238

Cheap flight deals from Caribbean Islands to Massachusetts

Keep the following information in mind while searching for Caribbean Islands to Massachusetts flight deals. Data was last updated November 14, 2025.

Round-trip from

$228
(Kiwi.com)

One-way from

$78
(Cheapflightsfares)
From Caribbean Islands to Massachusetts
Search Deals
One-way flight from Caribbean Islands to Massachusetts
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Massachusetts 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 14, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Massachusetts that are best for you.

Fly from

Caribbean Islands

Fly to

Massachusetts

Route

Depart

Return

Price

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Wed 12/24

2:34 pm-5:56 pm

Nonstop4h 22m

Boston Logan Intl

Tue 12/30

8:20 am-1:24 pm

Nonstop4h 04m

$229

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Wed 12/24

1:07 pm-5:55 pm

1 stop5h 48m

Boston Logan Intl

Tue 12/30

7:10 am-12:12 pm

Nonstop4h 02m

$229

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Mon 12/22

2:34 pm-5:56 pm

Nonstop4h 22m

Boston Logan Intl

Wed 12/31

8:20 am-1:24 pm

Nonstop4h 04m

$234

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Tue 12/23

2:34 pm-5:56 pm

Nonstop4h 22m

Boston Logan Intl

Tue 12/30

8:20 am-1:24 pm

Nonstop4h 04m

$234

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Wed 12/24

1:30 pm-11:33 pm

1 stop11h 03m

Boston Logan Intl

Tue 12/30

5:59 am-1:59 pm

1 stop7h 00m

$238

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 12/16

3:55 am-9:52 am

1 stop30h 57m

Boston Logan Intl

Fri 1/9

5:28 am-11:52 pm

1 stop17h 24m

$238

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Tue 12/23

6:00 am-9:08 am

Nonstop4h 08m

Hartford Bradley Intl

Tue 12/30

12:05 pm-1:34 am

1 stop12h 29m

$239

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 12/24

6:00 am-9:08 am

Nonstop4h 08m

Hartford Bradley Intl

Tue 12/30

12:05 pm-1:34 am

1 stop12h 29m

$239

OranjestadBoston

AUA - BOS

AUABOS

Oranjestad Reina Beatrix

Sat 12/6

4:40 pm-11:56 pm

1 stop8h 16m

Boston Logan Intl

Tue 12/9

5:45 am-3:35 pm

1 stop8h 50m

$246

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 11/21

5:04 pm-8:15 pm

Nonstop4h 11m

Boston Logan Intl

Sat 11/29

4:24 pm-9:29 pm

Nonstop4h 05m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Massachusetts (average of $56). Flying from Caribbean Islands to Massachusetts in October is currently the most expensive (average of $138). 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 EPX to MA?

Find hourly flight availability from Caribbean Islands to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 14, 2025.

It’s typically best to fly out from Caribbean Islands to Massachusetts at noon. Doing so could potentially save you 14% on the flight price compared to flying in the morning, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Massachusetts. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Caribbean Islands to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Caribbean Islands to Massachusetts

Explore weekly flight availability from Caribbean Islands to Massachusetts. 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 14, 2025.

The most flights from zzEPX to USMA are scheduled on a Thursday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated November 14, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Caribbean Islands to Massachusetts have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,017 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,051 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,139 reviews
Delta
7.9
Good
8,007 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

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

    Departing from Caribbean Islands to Massachusetts will take you 4h 08m. The distance from Caribbean Islands to Massachusetts is about 1669 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Caribbean Islands to Massachusetts one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $113. Frontier flights start at $123 while deals on JetBlue start at $123 one-way.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Massachusetts (average of $56). Flying from Caribbean Islands to Massachusetts in October is currently the most expensive (average of $138). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Caribbean Islands to Massachusetts

Discover the top 7 airlines that operate flights from Caribbean Islands to Massachusetts. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$76Average$308FlexibilityNo cancel feeOn-time65%
FrontierCheapest$86Average$259FlexibilityNo cancel feeOn-time62%
DeltaCheapest$141Average$434FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$181Average$485FlexibilityNo cancel feeOn-time62%
ArajetCheapest$194Average$421FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$208Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$338Average$476FlexibilityNo cancel feeOn-time71%

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