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Caribbean Islands

$82+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 24, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$153
(Flybillet)

One-way from

$82
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$299
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
Search Deals
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 24, 2025.

This Flybillet deal was found by Cheapflights users on 4/23. 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 Flybillet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/122:42 pmBOS - SJU
Nonstop3h 54mSpirit Airlines
Thu 6/199:30 amSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 4/23$153
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
Thu 7/179:15 amBDL - SJU
1 stop7h 31mSpirit Airlines
Mon 7/215:41 pmSJU - BDL
1 stop14h 29mSpirit Airlines
Deal found 4/22$184
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 4/269:05 pmBOS - SJU
1 stop12h 27mMultiple Airlines
Sun 5/116:30 amSJU - BOS
Nonstop4h 13mMultiple Airlines
Deal found 4/22$184
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Thu 5/1511:43 amBOS - SJU
Nonstop4h 01mFrontier
Sun 5/186:30 amSJU - BOS
Nonstop4h 13mFrontier
Deal found 4/23$193
This Kiwi.com deal was found by Cheapflights users on 4/23. 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
Sat 5/1011:55 amSJU - BDL
Nonstop4h 04mMultiple Airlines
Deal found 4/23$194
This eDestinos deal was found by Cheapflights users on 4/23. 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.
Sat 5/104:59 pmBDL - SJU
Nonstop3h 54mFrontier
Fri 5/1611:55 amSJU - BDL
Nonstop4h 04mFrontier
Deal found 4/23$212
This JetBlue deal was found by Cheapflights users on 4/23. 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 5/308:03 pmBDL - SJU
Nonstop3h 53mJetBlue
Wed 6/48:35 pmSJU - BDL
Nonstop3h 56mJetBlue
Deal found 4/23$258
This JetBlue deal was found by Cheapflights users on 4/23. 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 5/257:00 amBOS - SJU
Nonstop4h 01mJetBlue
Thu 6/55:01 amSJU - BOS
Nonstop4h 08mJetBlue
Deal found 4/23$264
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 5/85:06 amBDL - SJU
2 stops9h 54mAmerican Airlines
Wed 5/286:10 amSJU - BDL
2 stops9h 41mAmerican Airlines
Deal found 4/23$265
This Delta deal was found by Cheapflights users on 4/23. 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 10/78:10 amBOS - SJU
Nonstop4h 12mDelta
Wed 10/151:32 pmSJU - BOS
Nonstop4h 17mDelta
Deal found 4/23$266
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 6/115:45 amBOS - STT
1 stop7h 51mSpirit Airlines
Mon 6/233:03 pmSTT - BOS
1 stop8h 44mSpirit Airlines
Deal found 4/23$266
This United Airlines deal was found by Cheapflights users on 4/23. 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 5/71:02 pmBDL - SJU
1 stop10h 52mUnited Airlines
Fri 5/91:05 amSJU - BDL
2 stops13h 10mUnited Airlines
Deal found 4/23$270

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 24, 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

Thu 6/12

2:42 pm-6:36 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Thu 6/19

9:30 am-1:37 pm

Nonstop4h 07m

$153

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 4/26

9:05 pm-9:32 am

1 stop12h 27m

San Juan Luis Munoz Marin Intl

Sun 5/11

6:30 am-10:43 am

Nonstop4h 13m

$184

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Thu 7/17

9:15 am-4:46 pm

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Mon 7/21

5:41 pm-8:10 am

1 stop14h 29m

$184

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

$193

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 4/26

2:53 pm-11:46 pm

1 stop8h 53m

San Juan Luis Munoz Marin Intl

Sat 5/10

11:55 am-3:59 pm

Nonstop4h 04m

$194

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 5/10

4:59 pm-8:53 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Fri 5/16

11:55 am-3:59 pm

Nonstop4h 04m

$212

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 5/30

8:03 pm-11:56 pm

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

Wed 6/4

8:35 pm-12:31 am

Nonstop3h 56m

$258

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 5/25

11:10 am-3:10 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 6/6

6:00 am-10:08 am

Nonstop4h 08m

$264

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Thu 5/8

5:06 am-3:00 pm

2 stops9h 54m

San Juan Luis Munoz Marin Intl

Wed 5/28

6:10 am-3:51 pm

2 stops9h 41m

$265

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 6/11

5:45 am-1:36 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

Mon 6/23

3:03 pm-11:47 pm

1 stop8h 44m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 24, 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.

Weekly flight availability from Massachusetts to Caribbean Islands

Explore weekly flight availability from Massachusetts to Caribbean Islands. 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 24, 2025.

The most flights from USMA to zzEPX 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 (7 on average).

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 24, 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
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

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
9,918 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

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
4,286 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

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
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

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.
SWISS
7.5
Good
1,582 reviews
Delta
8.0
Very good
7,920 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

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 Spirit Airlines ($82), Frontier ($96), and Southwest ($133).

  • 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 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$84Average$456FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$496FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$143Average$550FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$204Average$549FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$266Average$790FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$282Average$603FlexibilityNo 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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