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$77+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
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Cheap 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 December 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/29. 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 12/29$243
This eDestinos deal was found by Cheapflights users on 12/30. 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 12/30$250
This Expedia deal was found by Cheapflights users on 12/29. 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.
Tue 12/308:35 pmSJU - BOS
Nonstop4h 12mMultiple Airlines
Thu 1/17:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Deal found 12/29$282
This Priceline deal was found by Cheapflights users on 12/29. 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.
Tue 12/307:44 pmSJU - BDL
Nonstop4h 15mMultiple Airlines
Sun 1/410:03 amBDL - SJU
Nonstop3h 56mMultiple Airlines
Deal found 12/29$283
This Cheapflightsfares deal was found by Cheapflights users on 12/29. 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 12/316:00 amSJU - BDL
Nonstop4h 08mFrontier
Sat 1/310:03 amBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/29$284
This Priceline deal was found by Cheapflights users on 12/30. 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.
Tue 12/308:35 pmSJU - BOS
Nonstop4h 12mMultiple Airlines
Wed 1/77:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Deal found 12/30$289
This Expedia deal was found by Cheapflights users on 12/29. 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.
Tue 12/302:05 amSJU - BOS
Nonstop4h 09mMultiple Airlines
Wed 1/77:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Deal found 12/29$292
This Mytrip deal was found by Cheapflights users on 12/29. 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 12/306:00 amSJU - BDL
Nonstop4h 08mFrontier
Tue 1/67:03 pmBDL - SJU
Nonstop3h 56mFrontier
Deal found 12/29$309
This eDestinos deal was found by Cheapflights users on 12/30. 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
Mon 1/57:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Deal found 12/30$318
This Expedia deal was found by Cheapflights users on 12/30. 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.
Tue 12/308:35 pmSJU - BOS
Nonstop4h 12mJetBlue
Wed 1/78:20 pmBOS - SJU
Nonstop4h 02mJetBlue
Deal found 12/30$322
This Delta deal was found by Cheapflights users on 12/30. 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 12/312:45 pmSJU - BOS
1 stop8h 44mDelta
Tue 1/68:05 amBOS - SJU
Nonstop4h 06mDelta
Deal found 12/30$327
This Frontier deal was found by Cheapflights users on 12/31. 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.
Wed 12/319:37 pmSJU - BOS
1 stop13h 15mFrontier
Tue 1/612:31 pmBOS - SJU
Nonstop3h 59mFrontier
Deal found 12/31$330

Find 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 December 31, 2025.

Round-trip from

$112
(Expedia)

One-way from

$77
(Kiwi.com)
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 December 31, 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

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 1/22

10:52 am-2:12 pm

Nonstop4h 20m

Boston Logan Intl

Sat 1/24

3:18 pm-8:24 pm

Nonstop4h 06m

$135

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Sat 1/17

10:52 am-2:12 pm

Nonstop4h 20m

Boston Logan Intl

Mon 1/19

3:18 pm-8:24 pm

Nonstop4h 06m

$138

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

$155

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

3:43 pm-11:33 pm

1 stop6h 50m

$156

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 3/4

11:22 am-2:43 pm

Nonstop4h 21m

Boston Logan Intl

Tue 3/10

8:01 pm-12:08 am

Nonstop4h 07m

$167

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Mon 2/9

10:52 am-2:12 pm

Nonstop4h 20m

Boston Logan Intl

Tue 2/10

3:18 pm-8:24 pm

Nonstop4h 06m

$168

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 1/13

6:15 am-9:25 am

Nonstop4h 10m

Boston Logan Intl

Tue 1/20

3:43 pm-11:33 pm

1 stop6h 50m

$171

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-11:59 pm

1 stop13h 07m

Boston Logan Intl

Sun 3/1

12:43 pm-11:09 pm

1 stop9h 26m

$176

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 2/4

6:00 am-2:38 pm

1 stop9h 38m

Boston Logan Intl

Mon 2/9

3:43 pm-11:33 pm

1 stop6h 50m

$177

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 2/11

5:25 pm-4:55 pm

1 stop24h 30m

Hartford Bradley Intl

Sun 2/15

7:55 pm-12:46 am

Nonstop3h 51m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

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 $55). Flying from Caribbean Islands 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 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 December 31, 2025.

It’s typically best to fly out from Caribbean Islands 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 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 December 27, 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 December 31, 2025.

The most flights from zzEPX to USMA are scheduled on a Wednesday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 31, 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
8,013 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Comfort

7.9

Boarding

8.1

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
8,013 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Comfort

7.9

Boarding

8.1

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
9,128 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Comfort

7.9

Boarding

8.1

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
11,070 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Comfort

7.9

Boarding

8.1

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
2,903 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Comfort

7.9

Boarding

8.1

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
8,253 reviews
Delta
7.9
Good
8,013 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Comfort

7.9

Boarding

8.1

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 15m. 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 Frontier, which is currently one of the cheapest options available, starting at $53. Spirit Airlines flights start at $69 while deals on JetBlue start at $111 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 $55). Flying from Caribbean Islands 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 Islands 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 Islands to Massachusetts

Discover the top 8 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 December 31, 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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