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Massachusetts

$100+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Aug 8 — Aug 151
Fri 8/8
Fri 8/15
1 adult, Economy
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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 August 3, 2025.

Round-trip from

$176
(eDestinos)

One-way from

$100
(Kiwi.com)
From Caribbean Islands to Massachusetts
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One-way flight from Caribbean Islands to Massachusetts
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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 August 3, 2025.

This eDestinos deal was found by Cheapflights users on 8/1. 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 8/202:11 amSJU - BDL
1 stop9h 10mSpirit Airlines
Mon 8/2512:53 pmBDL - SJU
1 stop8h 55mSpirit Airlines
Deal found 8/1$176
This eDestinos deal was found by Cheapflights users on 8/1. 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.
Fri 9/1211:59 amSJU - BOS
1 stop11h 58mSpirit Airlines
Mon 9/152:53 pmBOS - SJU
1 stop10h 01mSpirit Airlines
Deal found 8/1$194
This Trip.com deal was found by Cheapflights users on 8/1. 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.
Thu 8/143:51 pmSJU - BOS
1 stop16h 44mMultiple Airlines
Wed 9/1012:20 pmBOS - SJU
1 stop8h 36mMultiple Airlines
Deal found 8/1$209
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/124:43 pmSJU - ALB
2 stops19h 10mAmerican Airlines
Sat 9/206:00 amALB - SJU
2 stops17h 37mAmerican Airlines
Deal found 8/2$215
This eDestinos deal was found by Cheapflights users on 8/1. 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 8/202:11 amSJU - BDL
1 stop9h 10mMultiple Airlines
Mon 8/259:09 pmBDL - SJU
Nonstop3h 55mMultiple Airlines
Deal found 8/1$233
This Trip.com deal was found by Cheapflights users on 8/2. 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.
Fri 8/86:00 amSJU - BOS
Nonstop4h 07mJetBlue
Tue 8/128:45 pmBOS - SJU
Nonstop4h 04mJetBlue
Deal found 8/2$234
This eDestinos deal was found by Cheapflights users on 8/1. 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 8/2110:04 amSJU - BDL
1 stop24h 45mFrontier
Sun 8/319:09 pmBDL - SJU
Nonstop3h 55mFrontier
Deal found 8/1$236
This Delta deal was found by Cheapflights users on 8/1. 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.
Fri 9/121:25 pmSJU - BOS
Nonstop4h 05mDelta
Mon 9/158:10 amBOS - SJU
Nonstop4h 05mDelta
Deal found 8/1$244
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:00 amSJU - BOS
1 stop9h 12mAmerican Airlines
Fri 10/107:30 amBOS - SJU
1 stop16h 29mAmerican Airlines
Deal found 7/31$253
This Frontier deal was found by Cheapflights users on 8/2. 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.
Thu 8/218:13 pmSJU - BOS
1 stop12h 22mFrontier
Mon 8/2511:08 amBOS - SJU
1 stop8h 00mFrontier
Deal found 8/2$264
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:05 pmSJU - BDL
2 stops16h 27mAmerican Airlines
Tue 9/235:15 amBDL - SJU
2 stops9h 38mAmerican Airlines
Deal found 7/31$267
This Delta deal was found by Cheapflights users on 8/1. 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.
Fri 9/122:15 pmSJU - ALB
1 stop9h 05mDelta
Sat 9/206:00 amALB - SJU
1 stop6h 59mDelta
Deal found 8/1$278

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 August 3, 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 JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 8/20

2:11 am-11:21 am

1 stop9h 10m

Hartford Bradley Intl

Mon 8/25

12:53 pm-9:48 pm

1 stop8h 55m

$176

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 9/12

11:59 am-11:57 pm

1 stop11h 58m

Boston Logan Intl

Mon 9/15

2:53 pm-12:54 am

1 stop10h 01m

$194

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 8/14

3:51 pm-8:35 am

1 stop16h 44m

Boston Logan Intl

Wed 9/10

12:20 pm-8:56 pm

1 stop8h 36m

$209

San JuanAlbany

SJU - ALB

SJUALB

San Juan Luis Munoz Marin Intl

Fri 9/12

4:43 pm-11:53 am

2 stops19h 10m

Albany Intl

Sat 9/20

6:00 am-11:37 pm

2 stops17h 37m

$215

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Wed 8/20

2:11 am-11:21 am

1 stop9h 10m

Hartford Bradley Intl

Mon 8/25

9:09 pm-1:04 am

Nonstop3h 55m

$233

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 8/8

6:00 am-10:07 am

Nonstop4h 07m

Boston Logan Intl

Tue 8/12

8:45 pm-12:49 am

Nonstop4h 04m

$234

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 8/21

10:04 am-10:49 am

1 stop24h 45m

Hartford Bradley Intl

Sun 8/31

9:09 pm-1:04 am

Nonstop3h 55m

$236

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 9/12

1:25 pm-5:30 pm

Nonstop4h 05m

Boston Logan Intl

Mon 9/15

8:10 am-12:15 pm

Nonstop4h 05m

$244

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 10/7

7:00 am-4:12 pm

1 stop9h 12m

Boston Logan Intl

Fri 10/10

7:30 am-11:59 pm

1 stop16h 29m

$253

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 8/21

8:13 pm-8:35 am

1 stop12h 22m

Boston Logan Intl

Mon 8/25

11:08 am-7:08 pm

1 stop8h 00m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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, January is the cheapest month in which you can book a flight from Caribbean Islands to Massachusetts (average of $218). Flying from Caribbean Islands 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 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 August 3, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Massachusetts as you normally would.

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 August 3, 2025.

The most flights from zzEPX to USMA are scheduled on a Saturday (31 on average). You will have fewer flight options on Wednesday, 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 August 3, 2025.
See what other customers who have flown with Southwest, Delta, and Copa 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.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,985 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,496 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,905 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $100. Frontier flights start at $112 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, January is the cheapest month in which you can book a flight from Caribbean Islands to Massachusetts (average of $218). Flying from Caribbean Islands 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 Islands 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 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 August 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$252FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$295FlexibilityNo cancel feeOn-time65%
DeltaCheapest$129Average$414FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$133Average$461FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$207Average$384FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$319Average$490FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$338Average$489FlexibilityNo cancel feeOn-time71%

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