HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$99+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean Islands to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$165
(SmartFares)

One-way from

$99
(Frontier)
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 June 12, 2025.

This SmartFares deal was found by Cheapflights users on 6/11. 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.
Thu 6/269:30 amSJU - BOS
Nonstop4h 07mSpirit Airlines
Sun 6/299:44 amBOS - SJU
1 stop11h 20mSpirit Airlines
Deal found 6/11$165
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
Thu 9/183:40 amSJU - BDL
1 stop8h 46mFrontier
Fri 9/261:11 pmBDL - SJU
1 stop13h 23mFrontier
Deal found 6/12$180
This Priceline deal was found by Cheapflights users on 6/10. 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.
Wed 8/2712:59 amSJU - BOS
1 stop7h 43mFrontier
Sun 8/3110:36 amBOS - SJU
1 stop13h 18mFrontier
Deal found 6/10$183
This Priceline deal was found by Cheapflights users on 6/11. 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.
Wed 7/212:59 amSJU - BOS
1 stop7h 07mMultiple Airlines
Tue 7/86:15 amBOS - SJU
1 stop13h 04mMultiple Airlines
Deal found 6/11$186
This SmartFares deal was found by Cheapflights users on 6/10. 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.
Thu 8/215:41 pmSJU - BDL
1 stop14h 29mSpirit Airlines
Sat 9/209:15 amBDL - SJU
1 stop7h 31mSpirit Airlines
Deal found 6/10$198
This CheapOair deal was found by Cheapflights users on 6/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:41 pmSJU - BDL
1 stop14h 29mMultiple Airlines
Mon 9/19:09 pmBDL - SJU
Nonstop3h 55mMultiple Airlines
Deal found 6/10$208
This Delta deal was found by Cheapflights users on 6/11. 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.
Thu 9/251:27 pmSJU - BOS
Nonstop4h 12mDelta
Tue 9/308:10 amBOS - SJU
Nonstop4h 05mDelta
Deal found 6/11$218
This JetBlue deal was found by Cheapflights users on 6/10. 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 6/266:00 amSJU - BOS
Nonstop4h 07mJetBlue
Sat 7/1210:10 amBOS - SJU
Nonstop4h 05mJetBlue
Deal found 6/10$226
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:05 amSJU - BOS
1 stop8h 09mUnited Airlines
Sun 11/96:00 amBOS - SJU
1 stop7h 40mUnited Airlines
Deal found 6/11$227
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 10/16:10 amSJU - ALB
2 stops17h 39mAmerican Airlines
Tue 10/75:28 amALB - SJU
2 stops10h 52mAmerican Airlines
Deal found 6/10$251
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/912:10 pmMBJ - BOS
1 stop6h 24mSpirit Airlines
Mon 7/288:39 pmBOS - MBJ
1 stop15h 26mSpirit Airlines
Deal found 6/10$258
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/301:05 amSJU - ALB
2 stops13h 12mUnited Airlines
Tue 10/76:00 amALB - SJU
2 stops14h 38mUnited Airlines
Deal found 6/10$271

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 June 12, 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 6/26

9:30 am-1:37 pm

Nonstop4h 07m

Boston Logan Intl

Sun 6/29

9:44 am-9:04 pm

1 stop11h 20m

$165

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 9/18

3:40 am-12:26 pm

1 stop8h 46m

Hartford Bradley Intl

Fri 9/26

1:11 pm-2:34 am

1 stop13h 23m

$180

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Wed 8/27

12:59 am-8:42 am

1 stop7h 43m

Boston Logan Intl

Sun 8/31

10:36 am-11:54 pm

1 stop13h 18m

$183

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 6/26

9:30 am-1:37 pm

Nonstop4h 07m

Boston Logan Intl

Sun 6/29

12:55 pm-12:44 am

1 stop11h 49m

$185

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 8/21

5:41 pm-8:10 am

1 stop14h 29m

Hartford Bradley Intl

Sat 9/20

9:15 am-4:46 pm

1 stop7h 31m

$198

San JuanHartford

SJU - BDL

SJUBDL

San Juan Luis Munoz Marin Intl

Thu 8/21

5:41 pm-8:10 am

1 stop14h 29m

Hartford Bradley Intl

Mon 9/1

9:09 pm-1:04 am

Nonstop3h 55m

$208

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Fri 7/4

1:33 pm-5:44 pm

Nonstop4h 11m

Boston Logan Intl

Sun 7/6

8:15 am-12:23 pm

Nonstop4h 08m

$218

San JuanBoston

SJU - BOS

SJUBOS

San Juan Luis Munoz Marin Intl

Thu 6/26

6:00 am-10:07 am

Nonstop4h 07m

Boston Logan Intl

Sat 7/12

10:10 am-2:15 pm

Nonstop4h 05m

$226

Montego BayBoston

MBJ - BOS

MBJBOS

Montego Bay Sangster Intl

Wed 7/9

12:10 pm-7:34 pm

1 stop6h 24m

Boston Logan Intl

Mon 7/28

8:39 pm-11:05 am

1 stop15h 26m

$258

Punta CanaBoston

PUJ - BOS

PUJBOS

Punta Cana

Wed 7/23

3:25 pm-11:48 pm

1 stop8h 23m

Boston Logan Intl

Wed 7/30

6:10 am-2:30 pm

1 stop8h 20m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 60 results
1
2
3
...
6

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 June is currently the most expensive (average of $306). 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 June 12, 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 June 12, 2025.

The most flights from zzEPX to USMA are scheduled on a Monday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 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 June 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Avelo 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
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Copa Airlines
7.5
Good
1,451 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Overall

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $99. Spirit Airlines flights start at $102 while deals on JetBlue start at $109 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 June is currently the most expensive (average of $306). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to Seattle flights
John F Kennedy Intl to O'Hare Intl flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Los Angeles flights
Los Angeles to Seattle flights
Los Angeles to Newark flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Orlando flights
Newark to Miami flights
Newark to Los Angeles flights
LaGuardia to O'Hare Intl flights
LaGuardia to Miami flights
Newark to Seattle flights
John F Kennedy Intl to Seattle flights
O'Hare Intl to John F Kennedy Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
San Francisco to John F Kennedy Intl flights
Seattle to Los Angeles flights
LaGuardia to Fort Lauderdale flights
Newark to Orlando flights
San Francisco to Newark flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to San Francisco flights
Los Angeles to Honolulu flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Las Vegas flights
Newark to O'Hare Intl flights
O'Hare Intl to Seattle flights
Dallas/Fort Worth to Los Angeles flights
O'Hare Intl to Las Vegas flights
Los Angeles to LaGuardia flights
Newark to Las Vegas flights
Los Angeles to San Francisco flights
Hobby to Las Vegas flights
John F Kennedy Intl to Atlanta flights
LaGuardia to Denver flights
Los Angeles to Dallas/Fort Worth flights
Atlanta to John F Kennedy Intl flights
San Francisco to Seattle flights
Newark to Dallas/Fort Worth flights
Fort Lauderdale to LaGuardia flights
Atlanta to LaGuardia flights
O'Hare Intl to LaGuardia flights
Hobby to Seattle flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$251FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$69Average$323FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$482FlexibilityNo cancel feeOn-time62%
DeltaCheapest$133Average$425FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$207Average$397FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$346Average$495FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$349Average$505FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.