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Caribbean Islands

$93+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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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 August 2, 2025.

Round-trip from

$197
(Expedia)

One-way from

$93
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$238
From Massachusetts to Caribbean Islands
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One-way flight from Massachusetts to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 2, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/112:20 pmBOS - SJU
1 stop12h 24mSpirit Airlines
Thu 11/610:57 amSJU - BOS
1 stop12h 11mSpirit Airlines
Deal found 8/1$195
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/176:15 pmBDL - SJU
1 stop6h 41mSpirit Airlines
Wed 8/202:11 amSJU - BDL
1 stop9h 10mSpirit Airlines
Deal found 8/1$199
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/173:25 pmBOS - SJU
1 stop17h 40mMultiple Airlines
Wed 8/2012:59 amSJU - BOS
1 stop7h 43mMultiple Airlines
Deal found 8/1$199
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/298:45 pmBOS - SJU
Nonstop4h 04mJetBlue
Fri 9/57:55 pmSJU - BOS
Nonstop4h 02mJetBlue
Deal found 7/31$209
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/203:40 pmBDL - SJU
1 stop7h 00mSouthwest
Sun 9/285:45 amSJU - BDL
1 stop6h 15mSouthwest
Deal found 7/30$235
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/232:45 pmBDL - SJU
1 stop9h 12mMultiple Airlines
Wed 8/2711:17 amSJU - BDL
Nonstop4h 00mMultiple Airlines
Deal found 8/1$236
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:20 pmBDL - SJU
Nonstop3h 50mJetBlue
Fri 9/1212:30 pmSJU - BDL
Nonstop3h 54mJetBlue
Deal found 7/31$242
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:55 pmBOS - STT
1 stop16h 18mSpirit Airlines
Tue 9/910:49 amSTT - BOS
1 stop13h 08mSpirit Airlines
Deal found 7/31$242
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:00 amBDL - SJU
1 stop10h 33mDelta
Sat 11/17:15 amSJU - BDL
1 stop11h 20mDelta
Deal found 7/31$245
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:03 amBDL - SJU
Nonstop3h 56mFrontier
Sun 12/146:00 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 8/1$247
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.
Mon 8/185:36 amBDL - SJU
1 stop17h 13mAmerican Airlines
Wed 8/271:40 pmSJU - BDL
1 stop9h 45mAmerican Airlines
Deal found 7/31$268
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.
Sat 9/206:30 amBOS - STT
1 stop8h 48mAmerican Airlines
Sat 9/275:10 pmSTT - BOS
2 stops15h 12mAmerican Airlines
Deal found 7/31$311

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 August 2, 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 1/27

6:15 am-7:21 pm

1 stop12h 06m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:27 pm-8:34 pm

Nonstop4h 07m

$195

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 8/17

3:25 pm-9:05 am

1 stop17h 40m

San Juan Luis Munoz Marin Intl

Wed 8/20

12:59 am-8:42 am

1 stop7h 43m

$199

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 8/17

6:15 pm-12:56 am

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Wed 8/20

2:11 am-11:21 am

1 stop9h 10m

$199

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 8/29

8:45 pm-12:49 am

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Thu 9/4

7:50 pm-11:52 pm

Nonstop4h 02m

$209

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 9/20

3:40 pm-10:40 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Sun 9/28

5:45 am-12:00 pm

1 stop6h 15m

$235

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 8/23

2:45 pm-11:57 pm

1 stop9h 12m

San Juan Luis Munoz Marin Intl

Wed 8/27

11:17 am-3:17 pm

Nonstop4h 00m

$236

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 8/23

9:09 pm-1:04 am

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Wed 8/27

11:17 am-3:17 pm

Nonstop4h 00m

$240

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 9/5

5:20 pm-9:10 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 9/12

12:30 pm-4:24 pm

Nonstop3h 54m

$242

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 8/27

6:55 pm-11:13 am

1 stop16h 18m

Saint Thomas Island Cyril E King

Tue 9/9

10:49 am-11:57 pm

1 stop13h 08m

$242

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 10/24

6:00 am-4:33 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:15 am-6:35 pm

1 stop11h 20m

$245

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 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 August 2, 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 August 2, 2025.

The most flights from USMA to zzEPX are scheduled on a Thursday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated August 2, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Copa Airlines from Massachusetts to Caribbean Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
7,983 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
1,493 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
8,904 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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 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.

  • 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 Spirit Airlines ($93), JetBlue ($111), and American Airlines ($128).

  • 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

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Alternative routes for Massachusetts to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$375FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$97Average$389FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$136Average$555FlexibilityNo cancel feeOn-time62%
DeltaCheapest$140Average$483FlexibilityNo cancel feeOn-timeN/A
ArajetCheapest$171Average$337FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$188Average$660FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$544FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$255Average$520FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$288Average$590FlexibilityNo cancel feeOn-time71%
AviancaCheapest$292Average$539FlexibilityNo cancel feeOn-time71%

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