HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$82+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 17, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$157
(FlightHub)

One-way from

$82
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$298

Good round-trip deal

$220 or less

Good one-way deal

$147 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
Search Deals
From Massachusetts to Caribbean
Search Deals
One-way flight from Massachusetts to Caribbean
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Caribbean.
Search Deals
Price to beat on a one-way flight from Massachusetts to Caribbean.
Search Deals

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 April 17, 2025.

This FlightHub deal was found by Cheapflights users on 4/17. 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.
Wed 10/84:40 pmBOS - SJU
1 stop8h 31mSpirit Airlines
Wed 10/1512:55 pmSJU - BOS
1 stop10h 34mSpirit Airlines
Deal found 4/17$157
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Thu 5/111:43 amBOS - SJU
Nonstop4h 01mMultiple Airlines
Thu 5/81:33 amSJU - BOS
1 stop17h 25mMultiple Airlines
Deal found 4/17$179
This FlightHub deal was found by Cheapflights users on 4/17. 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 7/109:15 amBDL - SJU
1 stop7h 31mSpirit Airlines
Mon 7/145:41 pmSJU - BDL
1 stop14h 29mSpirit Airlines
Deal found 4/17$185
This SmartFares deal was found by Cheapflights users on 4/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:43 amBOS - SJU
Nonstop4h 01mFrontier
Thu 5/86:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 4/17$188
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 4/262:53 pmBDL - SJU
1 stop8h 53mMultiple Airlines
Tue 5/611:55 amSJU - BDL
Nonstop4h 04mMultiple Airlines
Deal found 4/16$194
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 5/54:59 pmBDL - SJU
Nonstop3h 54mFrontier
Sat 5/1011:55 amSJU - BDL
Nonstop4h 04mFrontier
Deal found 4/16$215
This JetBlue deal was found by Cheapflights users on 4/16. 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 5/98:03 pmBDL - SJU
Nonstop3h 53mJetBlue
Wed 5/148:35 pmSJU - BDL
Nonstop3h 56mJetBlue
Deal found 4/16$258
This Delta deal was found by Cheapflights users on 4/15. 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 5/208:20 amBOS - SJU
Nonstop4h 01mDelta
Tue 6/101:33 pmSJU - BOS
Nonstop4h 11mDelta
Deal found 4/15$264
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Wed 4/3012:20 pmBDL - SJU
1 stop11h 34mUnited Airlines
Tue 5/61:05 amSJU - BDL
2 stops13h 10mUnited Airlines
Deal found 4/16$265
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Tue 5/206:16 amBDL - SJU
1 stop6h 29mAmerican Airlines
Sat 5/3111:50 amSJU - BDL
1 stop11h 23mAmerican Airlines
Deal found 4/17$269
This JetBlue deal was found by Cheapflights users on 4/15. 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.
Thu 5/158:55 pmBOS - SJU
Nonstop4h 00mJetBlue
Tue 6/36:00 amSJU - BOS
Nonstop4h 08mJetBlue
Deal found 4/15$269
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/106:10 amBOS - STT
1 stop8h 44mSpirit Airlines
Wed 5/142:41 pmSTT - BOS
2 stops32h 48mSpirit Airlines
Deal found 4/17$269

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 April 17, 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

Sun 5/4

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 5/8

1:33 am-6:58 pm

1 stop17h 25m

$166

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/1

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Thu 5/8

1:33 am-6:58 pm

1 stop17h 25m

$179

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Thu 7/10

9:15 am-4:46 pm

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Mon 7/14

5:41 pm-8:10 am

1 stop14h 29m

$185

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 5/1

11:43 am-3:44 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Thu 5/8

6:30 am-10:43 am

Nonstop4h 13m

$188

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 4/27

5:45 am-4:15 pm

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 5/6

11:55 am-3:59 pm

Nonstop4h 04m

$194

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Mon 5/5

4:59 pm-8:53 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sat 5/10

11:55 am-3:59 pm

Nonstop4h 04m

$215

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 5/9

8:03 pm-11:56 pm

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

Wed 5/14

8:35 pm-12:31 am

Nonstop3h 56m

$258

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 5/20

7:00 am-11:01 am

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Thu 6/5

7:30 am-11:42 am

Nonstop4h 12m

$264

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Wed 4/30

12:20 pm-11:54 pm

1 stop11h 34m

San Juan Luis Munoz Marin Intl

Tue 5/6

1:05 am-2:15 pm

2 stops13h 10m

$265

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Tue 5/20

6:16 am-12:45 pm

1 stop6h 29m

San Juan Luis Munoz Marin Intl

Sat 5/31

11:50 am-11:13 pm

1 stop11h 23m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 60 results
1
2
3
...
6

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 April 17, 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 April 17, 2025.

The most flights from USMA to 0CB are scheduled on a Wednesday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 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 April 17, 2025.
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Copa Airlines
7.6
Good
1,409 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $82. Frontier flights start at $90 while deals on Southwest start at $133 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Fort Lauderdale flights
Newark to Orlando flights
LaGuardia to Fort Lauderdale flights
Newark to Cancún flights
John F Kennedy Intl to Miami flights
LaGuardia to Miami flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Heathrow flights
San Francisco to John F Kennedy Intl flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Miami flights
John F Kennedy Intl to Los Angeles flights
Los Angeles to Newark flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to John F Kennedy Intl flights
John F Kennedy Intl to Dallas/Fort Worth flights
Newark to Los Angeles flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to San Francisco flights
Newark to Heathrow flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to Haneda flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to LaGuardia flights
Newark to Las Vegas flights
John F Kennedy Intl to O'Hare Intl flights
O'Hare Intl to Las Vegas flights
John F Kennedy Intl to Charles de Gaulle flights
O'Hare Intl to Dallas/Fort Worth flights
Los Angeles to Honolulu flights
John F Kennedy Intl to Orlando flights
O'Hare Intl to LaGuardia flights
Newark to Seattle flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Los Angeles to Boston flights
LaGuardia to Dallas/Fort Worth flights
LaGuardia to Orlando flights
Newark to Charles de Gaulle flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Gatwick flights
O'Hare Intl to Cancún flights
John F Kennedy Intl to Seattle flights
LaGuardia to Atlanta flights
John F Kennedy Intl to Mexico City flights
Seattle to Los Angeles flights
George Bush Intcntl to Cancún flights
Los Angeles to Seattle flights
Fort Lauderdale to Newark flights

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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$85Average$454FlexibilityNo cancel feeOn-time65%
DeltaCheapest$141Average$497FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$142Average$549FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$544FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$266Average$791FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$282Average$602FlexibilityNo cancel feeOn-time71%
AviancaCheapest$292Average$518FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$520FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$427Average$794FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.