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$91+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$151
(Cheapflightsfares)

One-way from

$91
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$254

Good round-trip deal

$244 or less

Good one-way deal

$137 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
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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. 11% potential increase in price ($35 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Wed 10/84:40 pmBOS - SJU
1 stop8h 31mSpirit Airlines
Wed 10/1512:55 pmSJU - BOS
1 stop10h 34mSpirit Airlines
Deal found 4/30$155
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1511:43 amBOS - SJU
Nonstop4h 01mFrontier
Sun 5/186:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 4/30$179
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Fri 7/259:15 amBDL - SJU
1 stop7h 31mSpirit Airlines
Thu 7/315:41 pmSJU - BDL
1 stop14h 29mSpirit Airlines
Deal found 4/30$184
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/59:05 pmBOS - SJU
1 stop13h 27mMultiple Airlines
Thu 5/156:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/30$194
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/812:27 pmBDL - SJU
1 stop6h 40mMultiple Airlines
Sun 6/156:20 amSJU - BDL
Nonstop4h 02mMultiple Airlines
Deal found 4/30$197
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 6/111:38 amBDL - SJU
Nonstop3h 55mFrontier
Fri 6/66:36 amSJU - BDL
Nonstop4h 02mFrontier
Deal found 4/30$214
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 10/111:23 amBOS - SJU
2 stops8h 47mAmerican Airlines
Mon 10/612:00 pmSJU - BOS
1 stop12h 19mAmerican Airlines
Deal found 4/30$223
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:10 amBOS - SJU
Nonstop4h 05mDelta
Wed 9/171:27 pmSJU - BOS
Nonstop4h 12mDelta
Deal found 4/30$224
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/215:30 amBOS - SJU
1 stop7h 04mUnited Airlines
Mon 9/291:05 amSJU - BOS
1 stop8h 04mUnited Airlines
Deal found 4/30$233
This JetBlue deal was found by Cheapflights users on 4/30. 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 11/710:15 pmBOS - SJU
Nonstop4h 02mJetBlue
Thu 11/137:00 pmSJU - BOS
Nonstop4h 18mJetBlue
Deal found 4/30$234
This Priceline deal was found by Cheapflights users on 4/30. 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.
Tue 6/35:45 amBOS - STT
1 stop7h 51mSpirit Airlines
Tue 6/102:41 pmSTT - BOS
1 stop7h 09mSpirit Airlines
Deal found 4/30$263
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 5/185:44 amBDL - SJU
1 stop8h 56mAmerican Airlines
Fri 5/237:15 amSJU - BDL
1 stop17h 37mAmerican Airlines
Deal found 4/30$265

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 May 1, 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

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/29

9:46 am-8:02 pm

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Tue 6/3

1:59 am-9:09 am

1 stop7h 10m

$170

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/15

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Sun 5/18

6:30 am-10:43 am

Nonstop4h 13m

$179

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 7/25

9:15 am-4:46 pm

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Thu 7/31

5:41 pm-8:10 am

1 stop14h 29m

$184

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 5/5

9:05 pm-10:32 am

1 stop13h 27m

San Juan Luis Munoz Marin Intl

Thu 5/15

6:30 am-10:43 am

Nonstop4h 13m

$194

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 6/8

12:27 pm-7:07 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Sun 6/15

6:20 am-10:22 am

Nonstop4h 02m

$197

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 6/1

11:38 am-3:33 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Sun 6/8

6:36 am-10:38 am

Nonstop4h 02m

$214

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 6/3

5:45 am-1:36 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

Tue 6/10

2:41 pm-9:50 pm

1 stop7h 09m

$263

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 5/18

5:44 am-2:40 pm

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Fri 5/23

7:15 am-12:52 am

1 stop17h 37m

$265

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 6/1

8:03 pm-11:56 pm

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

Wed 6/4

4:00 pm-8:06 pm

Nonstop4h 06m

$266

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 5/15

6:00 am-4:20 pm

2 stops10h 20m

Saint Thomas Island Cyril E King

Tue 5/20

1:25 pm-10:49 pm

1 stop9h 24m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 December is currently the most expensive (average of $336). 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 May 1, 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 May 1, 2025.

The most flights from USMA to 0CB are scheduled on a Thursday (18 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 May 1, 2025.
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,972 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.5
Good
1,414 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 $91. Frontier flights start at $97 while deals on JetBlue start at $134 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 December is currently the most expensive (average of $336). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$459FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$494FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$145Average$550FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$156Average$734FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$204Average$551FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$282Average$599FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$529FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$520FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$402Average$787FlexibilityNo cancel feeOn-time63%

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