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$63+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Massachusetts to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

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 November 20, 2024.

This Frontier deal was found by Cheapflights users on 11/19. 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 12/912:59 pmBOS - SJU
1 stop12h 03mFrontier
Thu 12/125:26 amSJU - BOS
Nonstop4h 26mFrontier
Deal found 11/19$103
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/85:00 amBOS - SJU
1 stop14h 22mSpirit Airlines
Tue 12/109:13 pmSJU - BOS
1 stop13h 01mSpirit Airlines
Deal found 11/19$109
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/79:27 amBOS - SJU
Nonstop4h 05mMultiple Airlines
Sat 12/219:13 pmSJU - BOS
1 stop13h 16mMultiple Airlines
Deal found 11/19$112
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 12/48:27 pmBDL - SJU
Nonstop3h 58mFrontier
Sat 12/77:16 pmSJU - BDL
1 stop15h 36mFrontier
Deal found 11/19$126
This FlightHub deal was found by Cheapflights users on 11/19. 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 12/510:55 amBDL - SJU
1 stop14h 45mMultiple Airlines
Wed 1/158:43 pmSJU - BDL
1 stop21h 22mMultiple Airlines
Deal found 11/19$173
This JetBlue deal was found by Cheapflights users on 11/20. 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.
Tue 12/3110:50 pmBOS - SJU
Nonstop3h 58mJetBlue
Fri 1/178:00 amSJU - BOS
Nonstop4h 14mJetBlue
Deal found 11/20$195
This Delta deal was found by Cheapflights users on 11/20. 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.
Tue 12/108:10 amBOS - SJU
Nonstop4h 08mDelta
Tue 12/172:13 pmSJU - BOS
Nonstop4h 27mDelta
Deal found 11/20$213
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Sun 11/246:00 amBOS - SJU
2 stops8h 54mAmerican Airlines
Wed 11/275:50 amSJU - BOS
1 stop6h 58mAmerican Airlines
Deal found 11/19$214
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/109:30 amBOS - SJU
2 stops14h 06mUnited Airlines
Tue 12/172:05 amSJU - BOS
1 stop9h 06mUnited Airlines
Deal found 11/20$226
This CheapOair deal was found by Cheapflights users on 11/19. 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.
Wed 12/1812:35 pmBOS - STT
1 stop21h 04mSpirit Airlines
Tue 12/2411:44 amSTT - BOS
2 stops10h 23mSpirit Airlines
Deal found 11/19$231
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/74:44 pmBOS - STT
1 stop18h 00mAmerican Airlines
Fri 12/133:45 pmSTT - BOS
2 stops21h 31mAmerican Airlines
Deal found 11/19$234
This FlightHub deal was found by Cheapflights users on 11/19. 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.
Tue 12/106:00 amBDL - SJU
1 stop13h 22mSpirit Airlines
Tue 12/179:13 pmSJU - BDL
1 stop26h 29mSpirit Airlines
Deal found 11/19$236

Find flights from Massachusetts to Caribbean within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 1/28

10:03 am-3:07 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Wed 2/12

8:30 pm-8:07 am

1 stop12h 37m

$103

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 2/22

4:59 pm-3:50 am

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Wed 2/26

6:40 am-10:00 am

Nonstop4h 20m

$108

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 1/31

5:15 pm-12:37 am

1 stop6h 22m

San Juan Luis Munoz Marin Intl

Wed 2/5

5:35 am-9:03 am

Nonstop4h 28m

$110

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 1/12

3:49 pm-8:47 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Mon 1/13

6:00 am-5:08 pm

1 stop12h 08m

$123

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Thu 1/9

6:00 pm-9:35 am

1 stop14h 35m

San Juan Luis Munoz Marin Intl

Thu 1/16

11:54 am-3:13 pm

Nonstop4h 19m

$167

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 12/10

8:10 am-1:18 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

Tue 12/17

2:13 pm-5:40 pm

Nonstop4h 27m

$213

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 1/22

2:45 pm-10:22 pm

1 stop6h 37m

San Juan Luis Munoz Marin Intl

Mon 1/27

2:05 am-8:13 am

1 stop7h 08m

$222

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 1/10

6:00 pm-9:35 am

1 stop14h 35m

San Juan Luis Munoz Marin Intl

Wed 1/15

8:43 pm-5:05 pm

1 stop21h 22m

$230

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 12/18

12:35 pm-10:39 am

1 stop21h 04m

Saint Thomas Island Cyril E King

Wed 12/25

11:44 am-9:07 pm

2 stops10h 23m

$231

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 2/1

11:25 am-4:39 pm

Nonstop4h 14m

San Juan Luis Munoz Marin Intl

Sun 2/9

5:00 am-8:17 am

Nonstop4h 17m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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.

Travel insights for flights from Massachusetts to Caribbean

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

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 March is currently the most expensive (average of $335). 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 November 20, 2024.

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 November 20, 2024.

The most flights from USMA to 0CB are scheduled on a Tuesday (11 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 November 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,785 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Frontier, which is currently one of the cheapest options available, starting at $63. JetBlue flights start at $63 while deals on Spirit Airlines start at $74 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 March is currently the most expensive (average of $335). 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

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$334FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$412FlexibilityNo cancel feeOn-time65%
DeltaCheapest$146Average$497FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$147Average$590FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$200Average$530FlexibilityNo cancel feeOn-time70%
AviancaCheapest$242Average$505FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$244Average$583FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$263Average$616FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$299Average$788FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$487Average$841FlexibilityNo cancel feeOn-time63%
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