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Caribbean Islands

$75+ Cheap flights from Massachusetts to Caribbean Islands

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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
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Cheap flight deals from Massachusetts to Caribbean Islands

Keep the following information in mind while searching for Massachusetts to Caribbean Islands flight deals. Data was last updated April 3, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$136
(Cheapflightsfares)

One-way from

$75
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$298
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 Islands
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One-way flight from Massachusetts to Caribbean Islands
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Highest demand for flights based on searches. 12% potential increase in price ($36 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 April 2025
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Find flight deals from Massachusetts to Caribbean Islands

Cheapest flights from Massachusetts to Caribbean Islands
Explore the most affordable flight options available from Massachusetts to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 4/277:52 pmBOS - SJU
Nonstop4h 00mSpirit Airlines
Wed 4/305:10 pmSJU - BOS
1 stop7h 35mSpirit Airlines
Deal found 4/2$136
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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.
Sat 4/59:47 pmBDL - SJU
Nonstop3h 50mFrontier
Tue 4/811:02 amSJU - BDL
Nonstop4h 06mFrontier
Deal found 4/2$158
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 5/47:52 pmBOS - SJU
Nonstop4h 00mMultiple Airlines
Sun 5/116:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/2$162
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 4/911:16 amBOS - SJU
Nonstop3h 56mFrontier
Sat 4/126:00 amSJU - BOS
Nonstop4h 16mFrontier
Deal found 4/2$178
This FlightHub deal was found by Cheapflights users on 4/2. 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 4/84:21 pmBDL - SJU
Nonstop3h 50mMultiple Airlines
Thu 4/246:38 pmSJU - BDL
1 stop14h 49mMultiple Airlines
Deal found 4/2$199
This JetBlue Airways deal was found by Cheapflights users on 4/2. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/208:40 amBDL - SJU
1 stop8h 12mJetBlue
Sat 5/248:55 pmSJU - BDL
Nonstop3h 57mJetBlue
Deal found 4/2$253
This JetBlue deal was found by Cheapflights users on 4/2. 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.
Sun 5/48:00 amBOS - SJU
Nonstop4h 12mJetBlue
Fri 5/96:00 amSJU - BOS
Nonstop4h 08mJetBlue
Deal found 4/2$254
This CheapOair deal was found by Cheapflights users on 4/2. 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.
Mon 5/58:35 pmBOS - MBJ
1 stop15h 20mSpirit Airlines
Wed 5/1412:07 pmMBJ - BOS
1 stop10h 22mSpirit Airlines
Deal found 4/2$258
This Delta deal was found by Cheapflights users on 4/2. 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 5/108:20 amBOS - SJU
Nonstop4h 01mDelta
Fri 5/161:39 pmSJU - BOS
Nonstop4h 18mDelta
Deal found 4/2$259
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Wed 4/301:31 pmBOS - STT
2 stops20h 29mSpirit Airlines
Sat 5/311:05 amSTT - BOS
2 stops20h 13mSpirit Airlines
Deal found 4/2$264
This United Airlines deal was found by Cheapflights users on 4/1. 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 4/1$265
This American Airlines deal was found by Cheapflights users on 4/1. 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 8/248:37 amBDL - SJU
2 stops11h 38mAmerican Airlines
Fri 8/295:30 amSJU - BDL
1 stop11h 18mAmerican Airlines
Deal found 4/1$269

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Caribbean Islands 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 3, 2025.
Use the filters below to find and compare flights from Massachusetts to Caribbean Islands that are best for you.

Fly from

Massachusetts

Fly to

Caribbean Islands

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 4/27

7:52 pm-11:52 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 4/30

5:10 pm-12:45 am

1 stop7h 35m

$136

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 5/4

4:59 pm-8:53 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Thu 5/8

11:55 am-3:59 pm

Nonstop4h 04m

$160

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

Sun 5/11

6:30 am-10:43 am

Nonstop4h 13m

$162

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 4/9

11:16 am-3:12 pm

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Sat 4/12

6:00 am-10:16 am

Nonstop4h 16m

$178

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 5/4

4:59 pm-8:53 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Thu 5/8

8:12 pm-11:22 am

1 stop15h 10m

$179

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

Wed 4/30

7:00 pm-12:00 pm

2 stops17h 00m

$231

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Tue 5/20

8:40 am-4:52 pm

1 stop8h 12m

San Juan Luis Munoz Marin Intl

Sat 5/24

8:55 pm-12:52 am

Nonstop3h 57m

$253

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/4

8:00 am-12:12 pm

Nonstop4h 12m

San Juan Luis Munoz Marin Intl

Fri 5/9

6:00 am-10:08 am

Nonstop4h 08m

$254

BostonMontego Bay

BOS - MBJ

BOSMBJ

Boston Logan Intl

Mon 5/5

8:35 pm-10:55 am

1 stop15h 20m

Montego Bay Sangster Intl

Wed 5/14

12:07 pm-11:29 pm

1 stop10h 22m

$258

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 5/10

8:20 am-12:21 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Fri 5/16

1:39 pm-5:57 pm

Nonstop4h 18m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

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

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

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

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

Find hourly flight availability from Massachusetts to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 3, 2025.

When flying from Massachusetts to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 3, 2025.
See what other customers who have flown with Delta, Alaska Airlines and Southwest from Massachusetts to Caribbean Islands have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,897 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
9,825 reviews
Delta
8.0
Very good
7,897 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
4,274 reviews
Delta
8.0
Very good
7,897 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
7.6
Good
1,400 reviews
Delta
8.0
Very good
7,897 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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
8,619 reviews
Delta
8.0
Very good
7,897 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

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 Islands. 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 Islands one-way?

    The cheapest airlines for a one-way flight from Massachusetts to Caribbean Islands are Frontier ($75), Spirit Airlines ($77), and Delta ($123).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Caribbean Islands 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 Islands?

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

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 Islands

Discover the top 10 airlines that operate flights from Massachusetts to Caribbean Islands. 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$350FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$454FlexibilityNo cancel feeOn-time65%
DeltaCheapest$141Average$492FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$141Average$556FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$544FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$266Average$759FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$282Average$591FlexibilityNo cancel feeOn-time71%
AviancaCheapest$292Average$529FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$364Average$527FlexibilityNo cancel feeOn-time70%
SouthwestCheapest$427Average$790FlexibilityNo cancel feeOn-time63%

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