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$96+ Cheap flights from Massachusetts to Caribbean

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
1 adult, Economy
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Cheap flight deals from Massachusetts to Caribbean

Keep the following information in mind while searching for Massachusetts to Caribbean flight deals. Data was last updated June 30, 2025.

Round-trip from

$171
(Priceline)

One-way from

$96
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$304

Good round-trip deal

$294 or less

Good one-way deal

$168 or less
From Massachusetts to Caribbean
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One-way flight from Massachusetts to Caribbean
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Highest demand for flights based on searches. 10% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Massachusetts to Caribbean.
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Price to beat on a one-way flight from Massachusetts to Caribbean.
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Find flight deals from Massachusetts to Caribbean

Cheapest flights from Massachusetts to Caribbean
Explore the most affordable flight options available from Massachusetts to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2025.

This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2511:44 amBDL - SJU
1 stop15h 06mFrontier
Fri 8/294:24 pmSJU - BDL
Nonstop4h 00mFrontier
Deal found 6/30$171
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/310:03 amBOS - SJU
Nonstop4h 05mSpirit Airlines
Wed 8/63:50 pmSJU - BOS
1 stop7h 58mSpirit Airlines
Deal found 6/30$174
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2111:05 amBDL - SJU
1 stop15h 45mMultiple Airlines
Wed 8/272:11 amSJU - BDL
1 stop9h 10mMultiple Airlines
Deal found 6/30$186
This Priceline deal was found by Cheapflights users on 6/27. 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.
Thu 7/249:01 amBOS - SJU
1 stop14h 58mMultiple Airlines
Mon 7/281:21 amSJU - BOS
1 stop7h 16mMultiple Airlines
Deal found 6/27$198
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1812:53 pmBDL - SJU
1 stop8h 50mSpirit Airlines
Thu 8/214:12 pmSJU - BDL
1 stop7h 11mSpirit Airlines
Deal found 6/30$225
This Priceline deal was found by Cheapflights users on 6/27. 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.
Tue 7/19:01 amBOS - SJU
1 stop14h 58mFrontier
Sat 7/51:43 pmSJU - BOS
1 stop18h 09mFrontier
Deal found 6/27$227
This Cheapflightsfares deal was found by Cheapflights users on 6/29. 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 7/168:39 pmBOS - STT
1 stop13h 09mSpirit Airlines
Wed 7/2310:43 amSTT - BOS
1 stop8h 51mSpirit Airlines
Deal found 6/29$287
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/19:25 amBOS - STT
Nonstop3h 59mJetBlue
Sat 11/82:30 pmSTT - BOS
1 stop6h 01mJetBlue
Deal found 6/30$302
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Thu 10/26:00 amBOS - STT
2 stops10h 00mAmerican Airlines
Sat 10/45:10 pmSTT - BOS
2 stops15h 12mAmerican Airlines
Deal found 6/27$311
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 8/176:05 amBOS - PUJ
1 stop8h 55mSpirit Airlines
Sun 8/244:05 pmPUJ - BOS
1 stop7h 44mSpirit Airlines
Deal found 6/28$346
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:00 amBOS - PUJ
2 stops9h 25mAmerican Airlines
Fri 10/312:08 pmPUJ - BOS
1 stop8h 06mAmerican Airlines
Deal found 6/30$349
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2511:17 amBOS - PUJ
Nonstop4h 12mJetBlue
Sun 7/274:34 pmPUJ - BOS
Nonstop4h 06mJetBlue
Deal found 6/30$350

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Caribbean 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 30, 2025.
Use the filters below to find and compare flights from Massachusetts to Caribbean that are best for you.

Fly from

Massachusetts

Fly to

Caribbean

Route

Depart

Return

Price

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Mon 8/25

11:44 am-7:08 pm

1 stop7h 24m

San Juan Luis Munoz Marin Intl

Fri 8/29

4:24 pm-8:24 pm

Nonstop4h 00m

$171

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 8/3

10:03 am-2:08 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Wed 8/6

3:50 pm-11:48 pm

1 stop7h 58m

$174

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 7/24

9:01 am-11:59 pm

1 stop14h 58m

San Juan Luis Munoz Marin Intl

Mon 7/28

1:21 am-8:37 am

1 stop7h 16m

$198

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 7/11

6:00 am-4:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Wed 7/16

1:43 pm-7:52 am

1 stop18h 09m

$222

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 7/12

6:00 am-1:35 am

2 stops19h 35m

San Juan Luis Munoz Marin Intl

Wed 7/16

6:20 am-10:20 am

Nonstop4h 00m

$223

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Tue 7/22

6:20 am-1:35 am

2 stops19h 15m

San Juan Luis Munoz Marin Intl

Thu 7/31

10:14 pm-3:13 pm

1 stop16h 59m

$236

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 7/16

8:39 pm-9:48 am

1 stop13h 09m

Saint Thomas Island Cyril E King

Wed 7/23

10:43 am-7:34 pm

1 stop8h 51m

$287

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 9/8

6:29 pm-12:48 pm

2 stops18h 19m

Saint Thomas Island Cyril E King

Thu 9/11

1:40 pm-7:14 am

2 stops17h 34m

$311

BostonPunta Cana

BOS - PUJ

BOSPUJ

Boston Logan Intl

Sun 8/17

6:05 am-3:00 pm

1 stop8h 55m

Punta Cana

Sun 8/24

4:05 pm-11:49 pm

1 stop7h 44m

$346

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 9/17

5:35 am-1:33 pm

1 stop7h 58m

Saint Thomas Island Cyril E King

Wed 9/24

2:43 pm-1:18 am

1 stop10h 35m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Caribbean (average of $254). Flying from Massachusetts to Caribbean 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 CB?

Find hourly flight availability from Massachusetts to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 30, 2025.

When flying from Massachusetts to Caribbean, 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

Explore weekly flight availability from Massachusetts to Caribbean. 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 30, 2025.

The most flights from USMA to 0CB are scheduled on a Sunday (20 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated June 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Copa Airlines from Massachusetts to Caribbean. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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
7,969 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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
1,465 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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
8,852 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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.
JetBlue
7.3
Good
2,920 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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 Massachusetts to Caribbean. 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 one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $96. Frontier flights start at $99 while deals on Southwest start at $127 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Caribbean 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?

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

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

Discover the top 10 airlines that operate flights from Massachusetts to Caribbean. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$369FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$95Average$404FlexibilityNo cancel feeOn-time65%
ArajetCheapest$122Average$343FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$141Average$501FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$149Average$549FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$188Average$678FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$547FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$592FlexibilityNo cancel feeOn-time71%
AviancaCheapest$292Average$518FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$353Average$520FlexibilityNo cancel feeOn-time70%

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