Caribbean

$51+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Dez 26 — Jan 21
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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 Dezember 21, 2024.

Round-trip from

$106
(Frontier)

One-way from

$51
(Kiwi.com)
From Massachusetts to Caribbean
One-way flight from Massachusetts to Caribbean

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 Dezember 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/318:31 pmBDL - SJU
Nonstop3h 58mFrontier
Mi 1/153:27 pmSJU - BDL
Nonstop4h 07mFrontier
Deal found 12/21$149
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Di 12/316:00 amBOS - SJU
1 stop8h 41mFrontier
Mi 1/155:10 pmSJU - BOS
1 stop8h 20mFrontier
Deal found 12/20$193
This Justfly.com deal was found by Cheapflights users on 12/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/3112:43 pmBOS - SJU
Nonstop4h 10mSpirit Airlines
Mi 1/156:14 amSJU - BOS
1 stop10h 13mSpirit Airlines
Deal found 12/19$199
This Cheapflightsfares deal was found by Cheapflights users on 12/20. 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.
Di 12/3112:43 pmBOS - SJU
Nonstop4h 10mMultiple Airlines
Mi 1/156:00 amSJU - BOS
Nonstop4h 26mMultiple Airlines
Deal found 12/20$263
This JetBlue deal was found by Cheapflights users on 12/20. 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.
Di 12/3110:20 pmBDL - SJU
Nonstop3h 47mJetBlue
Mi 1/16:25 amSJU - BDL
Nonstop4h 05mJetBlue
Deal found 12/20$283
This Priceline deal was found by Cheapflights users on 12/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/316:00 amBDL - SJU
1 stop13h 22mMultiple Airlines
Sa 1/1111:55 amSJU - BDL
Nonstop4h 07mMultiple Airlines
Deal found 12/19$296
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/315:14 amBDL - SJU
1 stop18h 12mAmerican Airlines
Di 1/146:00 amSJU - BDL
1 stop10h 39mAmerican Airlines
Deal found 12/21$304
This American Airlines deal was found by Cheapflights users on 12/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 12/236:03 amBOS - STT
1 stop8h 12mAmerican Airlines
Mi 12/252:15 pmSTT - BOS
1 stop7h 42mAmerican Airlines
Deal found 12/20$320
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/3111:49 amBDL - SJU
1 stop10h 30mDelta
Mi 1/153:23 pmSJU - BDL
1 stop8h 40mDelta
Deal found 12/21$324
This United Airlines deal was found by Cheapflights users on 12/20. 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.
Di 12/314:45 pmBOS - SJU
1 stop12h 27mUnited Airlines
Di 1/142:05 amSJU - BOS
2 stops16h 18mUnited Airlines
Deal found 12/20$352
This American Airlines deal was found by Cheapflights users on 12/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 12/2511:06 amBOS - SJU
2 stops11h 04mAmerican Airlines
Fr 12/277:05 amSJU - BOS
1 stop12h 35mAmerican Airlines
Deal found 12/20$382
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 12/308:30 pmBOS - STT
1 stop16h 18mSpirit Airlines
Di 1/1411:51 amSTT - BOS
1 stop23h 45mSpirit Airlines
Deal found 12/21$398

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 2,558,603 searches. Data last updated Dezember 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sa 2/8

12:27 pm-9:41 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Mi 2/12

7:00 am-10:18 am

Nonstop4h 18m

$106

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mi 1/8

6:30 am-5:40 pm

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Mi 1/22

5:35 am-9:03 am

Nonstop4h 28m

$107

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Di 1/7

12:43 pm-5:53 pm

Nonstop4h 10m

San Juan Luis Munoz Marin Intl

Mi 1/15

6:14 am-3:27 pm

1 stop10h 13m

$115

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

So 1/19

4:01 pm-8:51 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sa 1/25

9:15 pm-9:55 am

1 stop13h 40m

$132

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Mo 2/10

6:00 pm-9:21 am

1 stop14h 21m

San Juan Luis Munoz Marin Intl

Sa 2/15

10:35 pm-10:40 am

1 stop13h 05m

$147

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Mi 2/19

11:17 am-11:22 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Mo 2/24

9:34 pm-10:22 am

1 stop13h 48m

$151

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sa 1/18

7:13 am-10:46 am

2 stops26h 33m

Saint Thomas Island Cyril E King

Fr 1/24

11:51 am-11:22 pm

2 stops12h 31m

$230

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mo 1/13

10:25 am-10:22 pm

2 stops10h 57m

San Juan Luis Munoz Marin Intl

Do 1/16

2:05 am-9:16 am

1 stop8h 11m

$232

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fr 1/17

11:25 am-4:39 pm

Nonstop4h 14m

San Juan Luis Munoz Marin Intl

Fr 1/24

8:00 am-11:14 am

Nonstop4h 14m

$243

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Do 1/30

7:13 pm-11:59 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Mi 2/5

1:50 pm-10:49 pm

1 stop9h 59m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

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 $380). 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 Dezember 21, 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 Dezember 21, 2024.

The most flights from USMA to 0CB are scheduled on a Monday (19 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (9 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 Dezember 21, 2024.
8.1
Very good
4,814 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,814 reviews
8.1
Very good
4,814 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,597 reviews
8.1
Very good
4,814 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,717 reviews
8.1
Very good
4,814 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.5
Good
1,922 reviews
8.1
Very good
4,814 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,266 reviews
8.1
Very good
4,814 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $51. Spirit Airlines flights start at $68 while deals on Delta start at $109 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 $380). 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.

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 Dezember 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$334FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$402FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$507FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$143Average$576FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$200Average$527FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$244Average$590FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$263Average$623FlexibilityNo cancel feeOn-time69%
AviancaCheapest$292Average$489FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$406Average$778FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$427Average$818FlexibilityNo cancel feeOn-time63%
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