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$75+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/308:00 amSJU - BOS
Nonstop4h 23mFrontier
Thu 1/112:18 pmBOS - SJU
Nonstop4h 04mFrontier
Deal found 12/26$146
This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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.
Tue 12/308:00 amSJU - BOS
Nonstop4h 23mFrontier
Sun 1/410:18 amBOS - SJU
Nonstop4h 04mFrontier
Deal found 12/27$155
This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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 12/296:00 amSJU - BDL
Nonstop4h 08mFrontier
Sun 1/117:03 pmBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/27$158
This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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 12/296:00 amSJU - BDL
Nonstop4h 08mFrontier
Sun 1/410:03 amBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/27$163
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/308:00 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Mon 1/57:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Deal found 12/26$174
This eDestinos deal was found by Cheapflights users on 12/27. 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.
Sun 12/286:00 amSJU - BDL
Nonstop4h 08mFrontier
Sun 1/410:03 amBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/27$176
This Cheapflightsfares deal was found by Cheapflights users on 12/27. 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 12/296:00 amSJU - BDL
Nonstop4h 08mFrontier
Wed 1/145:09 pmBDL - SJU
Nonstop3h 51mFrontier
Deal found 12/27$178
This eDestinos deal was found by Cheapflights users on 12/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:15 pmSJU - BOS
Nonstop4h 24mSpirit Airlines
Tue 1/67:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Deal found 12/26$179
This eDestinos deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:00 amSJU - BDL
Nonstop4h 08mFrontier
Sun 1/410:03 amBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/27$187
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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.
Sat 12/276:00 amSJU - BDL
Nonstop4h 08mFrontier
Tue 1/67:03 pmBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/26$188
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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.
Sat 12/276:00 amSJU - BDL
Nonstop4h 08mFrontier
Sun 1/410:03 amBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/26$193
This Frontier deal was found by Cheapflights users on 12/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:00 amSJU - BDL
Nonstop4h 08mFrontier
Sat 1/310:03 amBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/26$194

Find flight deals from Caribbean to Massachusetts

Keep the following information in mind while searching for Caribbean to Massachusetts flight deals. Data was last updated December 28, 2025.

Round-trip from

$134
(Kiwi.com)

One-way from

$75
(Expedia)

Popular in

July

Cheapest in

February

Average price

$246

Good round-trip deal

$124 or less

Good one-way deal

$129 or less
From Caribbean to Massachusetts
Search Deals
One-way flight from Caribbean to Massachusetts
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Caribbean to Massachusetts.
Search Deals
Price to beat on a one-way flight from Caribbean to Massachusetts.
Search Deals

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 December 28, 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 JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 1/23

10:52 am-2:12 pm

Nonstop4h 20m

Boston Logan Intl

Mon 1/26

3:18 pm-8:24 pm

Nonstop4h 06m

$135

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 1/15

3:01 pm-6:16 pm

Nonstop4h 15m

Hartford Bradley Intl

Sun 1/18

7:17 pm-12:08 am

Nonstop3h 51m

$141

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 3/5

3:55 pm-7:10 pm

Nonstop4h 15m

Hartford Bradley Intl

Tue 3/10

11:10 am-3:01 pm

Nonstop3h 51m

$156

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 2/6

10:52 am-2:12 pm

Nonstop4h 20m

Boston Logan Intl

Mon 2/9

7:00 am-11:33 pm

1 stop15h 33m

$156

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 2/11

3:55 pm-7:10 pm

Nonstop4h 15m

Hartford Bradley Intl

Wed 2/18

10:19 am-2:53 am

1 stop15h 34m

$160

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 2/13

3:55 pm-7:10 pm

Nonstop4h 15m

Hartford Bradley Intl

Sat 2/28

11:49 am-2:53 am

1 stop14h 04m

$167

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 1/23

6:00 am-2:38 pm

1 stop9h 38m

Boston Logan Intl

Sun 1/25

5:34 am-3:35 pm

1 stop9h 01m

$176

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sat 1/24

6:00 am-2:38 pm

1 stop9h 38m

Boston Logan Intl

Sat 1/31

3:43 pm-9:47 am

1 stop17h 04m

$176

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 2/5

7:15 pm-10:28 pm

Nonstop4h 13m

Boston Logan Intl

Sun 2/8

6:45 pm-11:48 pm

Nonstop4h 03m

$188

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 2/11

5:25 pm-10:17 am

1 stop17h 52m

Hartford Bradley Intl

Mon 2/16

7:55 pm-12:46 am

Nonstop3h 51m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

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 $55). Flying from Caribbean to Massachusetts in November is currently the most expensive (average of $141). 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 December 28, 2025.

It’s typically best to fly out from Caribbean to Massachusetts in the afternoon. Doing so could potentially save you 16% on the flight price compared to flying in the evening, 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 December 27, 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.

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 December 28, 2025.

The most flights from 0CB to USMA are scheduled on a Saturday (26 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (16 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 December 28, 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
8,019 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
8,019 reviews
Delta
7.9
Good
8,019 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
11,073 reviews
Delta
7.9
Good
8,019 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
2,901 reviews
Delta
7.9
Good
8,019 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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
8,211 reviews
Delta
7.9
Good
8,019 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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.
Frontier
5.8
Fair
3,065 reviews
Delta
7.9
Good
8,019 reviews

Boarding

8.1

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

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 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 Spirit Airlines, Frontier, and American Airlines fly from Caribbean to Massachusetts in about 4h 15m. The time it takes to get you to your destination can typically vary by up to 11h 01m. 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?

    $53 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and JetBlue, with prices starting from $69 and $111, 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 $55). Flying from Caribbean to Massachusetts in November is currently the most expensive (average of $141). 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$299FlexibilityNo cancel feeOn-time65%
FrontierCheapest$87Average$270FlexibilityNo cancel feeOn-time62%
DeltaCheapest$136Average$423FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$170Average$416FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$184Average$538FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$192Average$233FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$208Average$500FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$496FlexibilityNo cancel feeOn-time71%

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