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$100+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Round-trip from

$226
(eDestinos)

One-way from

$100
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$268

Good round-trip deal

$163 or less

Good one-way deal

$163 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. 17% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 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 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 November 6, 2025.

This eDestinos deal was found by Cheapflights users on 11/6. 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.
Thu 12/257:00 amSJU - BOS
1 stop19h 19mFrontier
Thu 1/16:00 amBOS - SJU
1 stop17h 37mFrontier
Deal found 11/6$226
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/2010:09 pmSJU - BOS
2 stops36h 33mMultiple Airlines
Sat 1/37:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Deal found 11/5$228
This Expedia deal was found by Cheapflights users on 11/5. 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.
Fri 12/263:15 pmSJU - BOS
Nonstop4h 24mSpirit Airlines
Wed 12/3112:29 pmBOS - SJU
1 stop8h 37mSpirit Airlines
Deal found 11/5$229
This eDestinos deal was found by Cheapflights users on 11/6. 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 12/226:00 amSJU - BOS
1 stop29h 07mFrontier
Thu 1/16:00 amBOS - SJU
1 stop17h 37mFrontier
Deal found 11/6$231
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/411:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Sun 12/78:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
Deal found 11/5$235
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/243:15 pmSJU - BOS
Nonstop4h 24mMultiple Airlines
Fri 1/210:57 amBOS - SJU
1 stop10h 47mMultiple Airlines
Deal found 11/5$236
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/297:06 pmSJU - BOS
2 stops40h 02mMultiple Airlines
Tue 1/67:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Deal found 11/5$237
This SmartFares deal was found by Cheapflights users on 11/5. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/216:01 amSJU - BDL
Nonstop4h 04mJetBlue
Sun 11/238:50 pmBDL - SJU
Nonstop3h 46mJetBlue
Deal found 11/5$238
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/410:42 amSJU - BOS
2 stops24h 40mMultiple Airlines
Sun 12/78:11 pmBOS - SJU
1 stop13h 22mMultiple Airlines
Deal found 11/4$238
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/224:21 pmSJU - BDL
1 stop19h 49mFrontier
Tue 1/610:48 amBDL - SJU
Nonstop3h 56mFrontier
Deal found 11/6$239
This Super.com deal was found by Cheapflights users on 11/6. 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.
Sun 12/214:10 amSJU - BOS
1 stop7h 40mSpirit Airlines
Wed 1/77:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Deal found 11/6$239
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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 12/223:15 pmSJU - BOS
Nonstop4h 24mSpirit Airlines
Thu 1/110:56 amBOS - SJU
1 stop14h 16mSpirit Airlines
Deal found 11/4$240

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 November 6, 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 1/22

1:58 pm-10:01 pm

1 stop9h 03m

Albany Intl

Mon 1/26

6:25 pm-1:08 pm

1 stop17h 43m

$235

San JuanAlbany

SJU - ALB

SJUALB

San Juan Luis Munoz Marin Intl

Thu 1/22

5:50 pm-11:41 pm

1 stop6h 51m

Albany Intl

Mon 1/26

5:45 am-1:17 pm

1 stop6h 32m

$235

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

$245

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 11/21

6:01 am-9:05 am

Nonstop4h 04m

Hartford Bradley Intl

Sun 11/23

8:50 pm-1:36 am

Nonstop3h 46m

$254

Saint Thomas IslandBoston

STT - BOS

STTBOS

Saint Thomas Island Cyril E King

Mon 12/22

1:30 pm-9:05 pm

1 stop8h 35m

Boston Logan Intl

Wed 12/31

6:01 am-1:51 pm

1 stop6h 50m

$254

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 12/19

6:00 am-9:08 am

Nonstop4h 08m

Hartford Bradley Intl

Sun 1/4

12:05 pm-11:15 pm

2 stops34h 10m

$262

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sun 12/21

4:34 pm-8:00 pm

Nonstop4h 26m

Boston Logan Intl

Sat 1/3

8:30 am-1:35 pm

Nonstop4h 05m

$262

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 12/5

2:20 pm-5:45 pm

Nonstop4h 25m

Boston Logan Intl

Mon 12/8

8:10 am-1:10 pm

Nonstop4h 00m

$262

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 11/14

2:27 pm-5:50 pm

Nonstop4h 23m

Boston Logan Intl

Mon 11/17

8:10 am-1:15 pm

Nonstop4h 05m

$262

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 11/12

2:05 am-2:11 pm

2 stops13h 06m

Hartford Bradley Intl

Tue 11/18

6:00 am-9:26 pm

2 stops14h 26m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, February is the cheapest month in which you can book a flight from Caribbean to Massachusetts (average of $56). Flying from Caribbean to Massachusetts in July is currently the most expensive (average of $137). 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 November 6, 2025.

It’s typically best to fly out from Caribbean 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 to Massachusetts?

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

Travelers seeking maximum savings on their Caribbean 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.

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 6, 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
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

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
8,001 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

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
11,040 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

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
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

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
8,122 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

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.
Frontier
5.8
Fair
3,115 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

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 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 American Airlines, United Airlines, and Delta fly from Caribbean to Massachusetts in about 4h 22m. The time it takes to get you to your destination can typically vary by up to 4h 41m. There are 1697 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?

    $116 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $118 and $120, 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, February is the cheapest month in which you can book a flight from Caribbean to Massachusetts (average of $56). Flying from Caribbean to Massachusetts in July is currently the most expensive (average of $137). 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 7 airlines flying from Caribbean to Massachusetts

Discover the top 7 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 November 6, 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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