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$68+ 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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$98
(Frontier)

One-way from

$68
(Trip.com)
From Caribbean Islands to Massachusetts
Search Deals
One-way flight from Caribbean Islands to Massachusetts
Search Deals

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 February 22, 2025.

This Frontier deal was found by Cheapflights users on 2/21. 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.
Fri 4/46:00 amSJU - BOS
Nonstop4h 16mFrontier
Mon 4/711:16 amBOS - SJU
Nonstop3h 56mFrontier
Deal found 2/21$98
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 3/1112:49 pmSJU - BOS
1 stop11h 10mSpirit Airlines
Tue 3/1810:43 amBOS - SJU
Nonstop4h 01mSpirit Airlines
Deal found 2/21$110
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Fri 5/1611:55 amSJU - BDL
Nonstop4h 04mFrontier
Sun 5/184:59 pmBDL - SJU
Nonstop3h 54mFrontier
Deal found 2/22$116
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 5/156:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Mon 5/196:00 amBOS - SJU
1 stop18h 12mMultiple Airlines
Deal found 2/21$121
This OneTravel deal was found by Cheapflights users on 2/20. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/289:34 pmSJU - BDL
1 stop13h 48mMultiple Airlines
Sat 3/89:40 pmBDL - SJU
Nonstop4h 50mMultiple Airlines
Deal found 2/20$147
This Mytrip deal was found by Cheapflights users on 2/21. 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 3/1112:30 amSJU - BDL
2 stops34h 11mSpirit Airlines
Mon 3/2410:45 amBDL - SJU
2 stops34h 11mSpirit Airlines
Deal found 2/21$157
This Delta deal was found by Cheapflights users on 2/20. 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 4/41:30 pmSJU - BOS
Nonstop4h 13mDelta
Sun 4/68:20 amBOS - SJU
Nonstop4h 00mDelta
Deal found 2/20$198
This Frontier deal was found by Cheapflights users on 2/21. 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.
Mon 3/172:15 pmPUJ - BOS
1 stop10h 29mFrontier
Mon 3/245:10 amBOS - PUJ
1 stop7h 50mFrontier
Deal found 2/21$213
This Delta deal was found by Cheapflights users on 2/21. 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 2/286:15 amSJU - BDL
1 stop10h 43mDelta
Mon 3/32:23 pmBDL - SJU
1 stop8h 23mDelta
Deal found 2/21$227
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/273:26 amSJU - BOS
Nonstop4h 09mJetBlue
Sun 3/27:35 pmBOS - SJU
Nonstop4h 07mJetBlue
Deal found 2/20$246
This FlightHub deal was found by Cheapflights users on 2/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2712:07 pmMBJ - BOS
1 stop8h 45mSpirit Airlines
Tue 4/82:10 pmBOS - MBJ
1 stop21h 45mSpirit Airlines
Deal found 2/22$247
This American Airlines deal was found by Cheapflights users on 2/20. 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 2/284:45 pmSJU - BOS
1 stop6h 59mAmerican Airlines
Sun 3/210:05 amBOS - SJU
1 stop12h 49mAmerican Airlines
Deal found 2/20$252

Find flights from Caribbean Islands to Massachusetts within your budget

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 February 22, 2025.

Fly from

Caribbean Islands

Fly to

Massachusetts

Route

Depart

Return

Price

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 4/4

6:00 am-10:16 am

Nonstop4h 16m

Boston Logan Intl

Mon 4/7

11:16 am-3:12 pm

Nonstop3h 56m

$98

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Tue 3/11

12:49 pm-11:59 pm

1 stop11h 10m

Boston Logan Intl

Tue 3/18

10:43 am-2:44 pm

Nonstop4h 01m

$110

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Fri 5/16

11:55 am-3:59 pm

Nonstop4h 04m

Hartford Bradley Intl

Sun 5/18

4:59 pm-8:53 pm

Nonstop3h 54m

$116

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 5/15

6:30 am-10:43 am

Nonstop4h 13m

Boston Logan Intl

Mon 5/19

6:00 am-12:12 am

1 stop18h 12m

$121

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Tue 3/11

12:30 am-10:41 am

2 stops34h 11m

Hartford Bradley Intl

Mon 3/24

10:45 am-8:56 pm

2 stops34h 11m

$157

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Tue 4/22

7:49 pm-9:40 am

1 stop13h 51m

Hartford Bradley Intl

Sun 4/27

4:25 pm-8:15 pm

Nonstop3h 50m

$161

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 4/4

1:30 pm-5:43 pm

Nonstop4h 13m

Boston Logan Intl

Sun 4/6

8:20 am-12:20 pm

Nonstop4h 00m

$198

Punta CanaBoston

PUJ - BOS

PUJBOS

Punta Cana

Mon 3/17

2:15 pm-12:44 am

1 stop10h 29m

Boston Logan Intl

Mon 3/24

5:10 am-1:00 pm

1 stop7h 50m

$213

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 2/27

5:50 pm-11:59 pm

1 stop7h 09m

Boston Logan Intl

Wed 3/5

10:15 am-10:22 pm

2 stops11h 07m

$219

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 2/27

3:26 am-6:35 am

Nonstop4h 09m

Boston Logan Intl

Sun 3/2

7:35 pm-12:42 am

Nonstop4h 07m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

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.

Travel insights for flights from Caribbean Islands to Massachusetts

Get recent, data-driven insights about flights from Caribbean Islands to Massachusetts including ideal travel times, pricing trends, and more.

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 February 22, 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 February 22, 2025.

The most flights from zzEPX to USMA are scheduled on a Thursday (26 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 February 22, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Alaska Airlines from Caribbean Islands to Massachusetts by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,702 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,502 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,789 reviews
Southwest
8.1
Very good
4,396 reviews

Overall

8.1

Comfort

8.1

Food

7.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier, which is currently one of the cheapest options available, starting at $68. Spirit Airlines flights start at $69 while deals on United Airlines start at $104 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$71Average$140FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$80Average$294FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$118Average$457FlexibilityNo cancel feeOn-time62%
DeltaCheapest$127Average$411FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$207Average$408FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$215Average$467FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$456FlexibilityNo cancel feeOn-time71%
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