HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$114+ Cheap flights from Massachusetts to Caribbean Islands

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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Caribbean Islands 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 Massachusetts to Caribbean Islands

Keep the following information in mind while searching for Massachusetts to Caribbean Islands flight deals. Data was last updated September 22, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$187
(Kiwi.com)

One-way from

$114
(Cheapflightsfares)

Popular in

December

Cheapest in

October

Average price

$263
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
Search Deals
From Massachusetts to Caribbean Islands
Search Deals
One-way flight from Massachusetts to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Massachusetts to Caribbean Islands

Cheapest flights from Massachusetts to Caribbean Islands
Explore the most affordable flight options available from Massachusetts to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:49 pmBOS - SJU
1 stop16h 15mSpirit Airlines
Tue 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/20$187
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:49 pmBOS - SJU
1 stop16h 15mSpirit Airlines
Sat 10/46:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/20$199
This Cheapflightsfares deal was found by Cheapflights users on 9/21. 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.
Fri 12/511:13 amBOS - SJU
1 stop11h 06mSpirit Airlines
Mon 12/86:00 amSJU - BOS
1 stop18h 25mSpirit Airlines
Deal found 9/21$205
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:49 pmBOS - SJU
1 stop16h 15mMultiple Airlines
Fri 10/37:50 pmSJU - BOS
1 stop17h 33mMultiple Airlines
Deal found 9/20$211
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/252:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Thu 10/3011:51 amSJU - BOS
1 stop12h 08mSpirit Airlines
Deal found 9/20$214
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
Tue 11/1810:57 amSJU - BOS
1 stop12h 11mSpirit Airlines
Deal found 9/20$215
This Priceline deal was found by Cheapflights users on 9/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Mon 11/33:48 amSJU - BOS
1 stop10h 32mSpirit Airlines
Deal found 9/21$217
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Sat 10/46:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/20$220
This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/68:00 amBOS - SJU
Nonstop4h 27mJetBlue
Thu 10/98:22 pmSJU - BOS
Nonstop4h 02mJetBlue
Deal found 9/22$223
This Priceline deal was found by Cheapflights users on 9/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/289:38 amBOS - SJU
1 stop13h 45mMultiple Airlines
Sat 10/46:44 amSJU - BOS
1 stop7h 04mMultiple Airlines
Deal found 9/21$226
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:49 pmBOS - SJU
1 stop16h 15mMultiple Airlines
Wed 10/81:26 pmSJU - BOS
1 stop18h 10mMultiple Airlines
Deal found 9/20$228
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/42:18 pmBOS - SJU
1 stop19h 34mMultiple Airlines
Fri 10/101:59 amSJU - BOS
1 stop29h 37mMultiple Airlines
Deal found 9/20$230

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Caribbean Islands 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 September 22, 2025.
Use the filters below to find and compare flights from Massachusetts to Caribbean Islands that are best for you.

Fly from

Massachusetts

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/24

6:00 pm-11:00 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Tue 3/10

5:15 am-9:23 am

Nonstop4h 08m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 12/7

12:55 pm-5:57 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:10 pm-10:18 pm

Nonstop4h 08m

$262

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 1/18

6:50 pm-11:56 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Sat 1/24

8:00 am-11:14 am

Nonstop4h 14m

$262

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 9/28

6:00 am-12:34 pm

1 stop6h 34m

San Juan Luis Munoz Marin Intl

Wed 10/1

4:55 pm-11:57 pm

1 stop7h 02m

$263

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 11/11

8:00 am-6:13 pm

1 stop9h 13m

San Juan Luis Munoz Marin Intl

Tue 11/18

12:30 pm-6:44 pm

1 stop7h 14m

$265

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 10/31

4:15 pm-8:10 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Sat 11/15

6:00 am-9:04 am

Nonstop4h 04m

$267

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 10/18

7:10 am-4:42 pm

1 stop9h 32m

San Juan Luis Munoz Marin Intl

Fri 10/24

6:00 am-10:29 pm

1 stop16h 29m

$267

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 11/8

4:15 pm-9:10 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Sat 11/15

6:00 am-9:04 am

Nonstop4h 04m

$280

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 11/8

4:10 pm-9:05 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Sun 11/16

6:01 am-9:04 am

Nonstop4h 03m

$280

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 10/20

8:15 am-12:21 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Mon 10/27

1:32 pm-5:45 pm

Nonstop4h 13m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/21

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

Best time to book a flight from Massachusetts to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Massachusetts 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 Massachusetts to Caribbean Islands

What is the cheapest month to book a flight from Massachusetts to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $254). Flying from Massachusetts to Caribbean Islands in June is currently the most expensive (average of $339). 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 MA to EPX?

Find hourly flight availability from Massachusetts to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 22, 2025.

When flying from Massachusetts to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Massachusetts to Caribbean Islands

Explore weekly flight availability from Massachusetts to Caribbean Islands. 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 September 22, 2025.

The most flights from USMA to zzEPX are scheduled on a Thursday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Caribbean Islands. 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 Massachusetts to Caribbean Islands?

    There are many flights that can get you from Massachusetts to Caribbean Islands in 4h. Fly via JetBlue, United Airlines, or Delta to get the fastest option. The distance between Massachusetts and Caribbean Islands is about 1678 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airlines for a one-way flight from Massachusetts to Caribbean Islands are JetBlue ($124), Spirit Airlines ($127), and American Airlines ($129).

  • Can I find deals for flights from Massachusetts to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Caribbean Islands.

  • Can I find deals for business class flights from Massachusetts to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Massachusetts to Caribbean Islands 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 Massachusetts to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $254). Flying from Massachusetts to Caribbean Islands in June is currently the most expensive (average of $339). 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 Massachusetts to Caribbean Islands

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

Top 10 airlines flying from Massachusetts to Caribbean Islands

Discover the top 10 airlines that operate flights from Massachusetts to Caribbean Islands. 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 September 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$82Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$379FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$136Average$551FlexibilityNo cancel feeOn-time62%
DeltaCheapest$143Average$480FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$188Average$655FlexibilityNo cancel feeOn-time67%
ArajetCheapest$192Average$359FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$192Average$412FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$194Average$538FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$590FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$560FlexibilityNo 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.