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$118+ Cheap flights from Caribbean 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Caribbean to Massachusetts

Keep the following information in mind while searching for Caribbean to Massachusetts flight deals. Data was last updated September 16, 2025.

Round-trip from

$171
(Cheapflightsfares)

One-way from

$118
(American Airlines)

Popular in

July

Cheapest in

January

Average price

$224

Good round-trip deal

$207 or less

Good one-way deal

$156 or less
From Caribbean to Massachusetts
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One-way flight from Caribbean to Massachusetts
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Highest demand for flights based on searches. 21% potential increase in price ($65 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 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 Caribbean to Massachusetts.
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Price to beat on a one-way flight from Caribbean to Massachusetts.
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Find flight deals from Caribbean to Massachusetts

Cheapest flights from Caribbean to Massachusetts
Explore the most affordable flight options available from Caribbean to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

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.
Wed 10/16:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Tue 10/72:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/14$171
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/33:55 pmSJU - BOS
1 stop9h 04mAmerican Airlines
Sat 10/410:10 amBOS - SJU
2 stops13h 27mAmerican Airlines
Deal found 9/14$210
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.
Thu 9/2511:59 amSJU - BOS
1 stop11h 58mSpirit Airlines
Tue 10/72:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/15$213
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.
Wed 10/292:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Mon 11/32:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/14$214
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2311:51 amSJU - BOS
1 stop12h 08mSpirit Airlines
Tue 10/282:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/15$217
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/282:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Wed 11/56:15 amBOS - SJU
1 stop12h 06mSpirit Airlines
Deal found 9/14$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.
Thu 9/2511:59 amSJU - BOS
1 stop11h 58mSpirit Airlines
Sat 9/2712:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Deal found 9/15$219
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Sat 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Deal found 9/15$228
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2911:59 amSJU - BOS
1 stop11h 58mSpirit Airlines
Thu 10/26:49 pmBOS - SJU
1 stop16h 15mSpirit Airlines
Deal found 9/15$230
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/212:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Mon 10/272:15 pmBOS - SJU
1 stop11h 29mSpirit Airlines
Deal found 9/15$231
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2511:59 amSJU - BOS
1 stop11h 58mSpirit Airlines
Tue 9/303:00 pmBOS - SJU
2 stops29h 56mSpirit Airlines
Deal found 9/15$232
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:30 pmSJU - ALB
1 stop6h 45mSouthwest
Tue 10/284:15 pmALB - SJU
1 stop6h 30mSouthwest
Deal found 9/15$235

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 September 16, 2025.
Use the filters below to find and compare flights from Caribbean to Massachusetts that are best for you.

Fly from

Caribbean

Fly to

Massachusetts

Route

Depart

Return

Price

San JuanAlbany

SJU - ALB

SJUALB

San Juan Luis Munoz Marin Intl

Thu 10/23

5:30 pm-12:15 am

1 stop6h 45m

Albany Intl

Tue 10/28

4:15 pm-10:45 pm

1 stop6h 30m

$235

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Sat 11/1

11:01 am-11:59 pm

1 stop12h 58m

Boston Logan Intl

Mon 11/3

8:24 pm-10:51 am

1 stop13h 27m

$253

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 10/24

6:33 pm-10:29 pm

Nonstop3h 56m

Hartford Bradley Intl

Sun 10/26

10:49 am-2:34 pm

Nonstop3h 45m

$254

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 10/24

2:25 pm-10:29 pm

1 stop8h 04m

Hartford Bradley Intl

Mon 10/27

10:49 am-2:34 pm

Nonstop3h 45m

$261

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 10/22

1:25 pm-10:29 pm

1 stop9h 04m

Hartford Bradley Intl

Sat 10/25

5:20 pm-9:10 pm

Nonstop3h 50m

$263

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 10/2

2:25 pm-10:29 pm

1 stop8h 04m

Hartford Bradley Intl

Mon 10/6

5:20 pm-9:10 pm

Nonstop3h 50m

$266

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 10/1

1:29 pm-10:29 pm

1 stop9h 00m

Hartford Bradley Intl

Mon 10/6

5:20 pm-9:10 pm

Nonstop3h 50m

$266

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 11/19

5:05 am-12:11 pm

1 stop8h 06m

Boston Logan Intl

Sun 11/23

10:55 pm-3:52 am

Nonstop3h 57m

$274

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Mon 2/2

6:00 am-9:05 am

Nonstop4h 05m

Hartford Bradley Intl

Sat 2/7

7:00 pm-11:51 pm

Nonstop3h 51m

$280

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Thu 12/4

1:33 pm-12:40 am

1 stop12h 07m

Boston Logan Intl

Sun 12/7

6:15 am-3:11 pm

1 stop7h 56m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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

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

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to Massachusetts (average of $218). Flying from Caribbean to Massachusetts in July is currently the most expensive (average of $311). 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 CB to MA?

Find hourly flight availability from Caribbean 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 September 16, 2025.

When flying from Caribbean to Massachusetts, 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 Caribbean to Massachusetts

Explore weekly flight availability from Caribbean 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 September 16, 2025.

The most flights from 0CB to USMA are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 September 16, 2025.
Read through reviews of airlines operating flights from Caribbean to Massachusetts, such as Delta, American Airlines, and JetBlue. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
JetBlue
7.2
Good
2,914 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Spirit Airlines
6.3
Okay
8,019 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Frontier
5.8
Fair
3,174 reviews
Delta
8.0
Very good
7,957 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

Related info for your journey

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

    Airlines like Southwest, Spirit Airlines, and JetBlue fly from Caribbean to Massachusetts in about 3h 56m. The time it takes to get you to your destination can typically vary by up to 9h 02m. There are 1669 mi between Caribbean and Massachusetts. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $118 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on American Airlines and Spirit Airlines, with prices starting from $118 and $132, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Caribbean to Massachusetts (average of $218). Flying from Caribbean to Massachusetts in July is currently the most expensive (average of $311). 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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Alternative routes for Caribbean to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Caribbean to Massachusetts

Discover the top 8 airlines that operate flights from Caribbean 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$257FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$136Average$421FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$140Average$465FlexibilityNo cancel feeOn-time62%
ArajetCheapest$199Average$393FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$207Average$384FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$208Average$486FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$338Average$496FlexibilityNo cancel feeOn-time71%

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