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Caribbean Islands

$65+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Massachusetts to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Caribbean Islands (zzEPX). 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 November 21, 2024.

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 November 21, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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.
Sun 12/89:52 amBOS - SJU
Nonstop4h 05mFrontier
Thu 12/125:05 pmSJU - BOS
1 stop8h 25mFrontier
Deal found 11/20$104
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/85:00 amBOS - SJU
1 stop14h 22mSpirit Airlines
Tue 12/109:13 pmSJU - BOS
1 stop13h 01mSpirit Airlines
Deal found 11/19$109
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Sun 12/89:52 amBOS - SJU
Nonstop4h 05mMultiple Airlines
Fri 12/139:13 pmSJU - BOS
1 stop13h 01mMultiple Airlines
Deal found 11/20$112
This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/128:27 pmBDL - SJU
Nonstop3h 58mFrontier
Mon 12/167:16 pmSJU - BDL
1 stop15h 36mFrontier
Deal found 11/21$124
This FlightHub deal was found by Cheapflights users on 11/21. 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.
Mon 12/96:00 amBDL - SJU
1 stop13h 22mMultiple Airlines
Mon 12/167:16 pmSJU - BDL
1 stop15h 36mMultiple Airlines
Deal found 11/21$166
This JetBlue deal was found by Cheapflights users on 11/20. 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.
Tue 12/3110:50 pmBOS - SJU
Nonstop3h 58mJetBlue
Fri 1/175:00 amSJU - BOS
Nonstop4h 17mJetBlue
Deal found 11/20$195
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Mon 11/256:00 amBOS - SJU
2 stops8h 43mAmerican Airlines
Sat 12/76:30 amSJU - BOS
1 stop14h 52mAmerican Airlines
Deal found 11/20$200
This Delta deal was found by Cheapflights users on 11/21. 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.
Tue 12/108:10 amBOS - SJU
Nonstop4h 08mDelta
Tue 12/172:13 pmSJU - BOS
Nonstop4h 27mDelta
Deal found 11/21$213
This United Airlines deal was found by Cheapflights users on 11/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/258:45 amBOS - SJU
2 stops11h 10mUnited Airlines
Wed 11/272:05 amSJU - BOS
1 stop6h 38mUnited Airlines
Deal found 11/21$214
This Mytrip deal was found by Cheapflights users on 11/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/810:34 amBOS - STT
2 stops25h 49mSpirit Airlines
Fri 12/1311:56 amSTT - BOS
1 stop13h 42mSpirit Airlines
Deal found 11/21$231
This JetBlue deal was found by Cheapflights users on 11/20. 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.
Fri 11/2910:20 pmBDL - SJU
Nonstop3h 44mJetBlue
Sat 12/76:04 amSJU - BDL
Nonstop3h 56mJetBlue
Deal found 11/20$239
This JetBlue deal was found by Cheapflights users on 11/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/97:00 amBOS - STT
1 stop5h 27mJetBlue
Fri 12/2012:52 pmSTT - BOS
1 stop6h 01mJetBlue
Deal found 11/21$239

Find flights from Massachusetts to Caribbean Islands within your budget

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 2/3

10:03 am-3:07 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Tue 2/11

5:07 pm-12:39 am

1 stop8h 32m

$104

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 12/9

9:51 am-2:56 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Tue 12/17

5:10 am-1:23 pm

1 stop9h 13m

$109

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 2/5

10:00 am-7:48 pm

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Sun 2/9

4:50 pm-11:22 pm

1 stop7h 32m

$124

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Thu 12/12

8:27 pm-1:25 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Mon 12/16

7:16 pm-9:52 am

1 stop15h 36m

$124

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Thu 1/23

6:00 pm-9:35 am

1 stop14h 35m

San Juan Luis Munoz Marin Intl

Mon 1/27

6:00 am-5:08 pm

1 stop12h 08m

$156

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 12/10

8:10 am-1:18 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

Mon 12/16

2:13 pm-5:40 pm

Nonstop4h 27m

$205

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Thu 1/9

10:30 pm-3:25 am

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Fri 1/17

8:00 am-11:14 am

Nonstop4h 14m

$213

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 12/7

3:57 pm-12:36 am

1 stop7h 39m

San Juan Luis Munoz Marin Intl

Mon 12/16

2:05 am-2:02 pm

2 stops12h 57m

$222

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Thu 1/23

6:00 pm-2:10 pm

2 stops19h 10m

San Juan Luis Munoz Marin Intl

Thu 1/30

10:09 pm-5:05 pm

1 stop19h 56m

$225

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 1/12

7:40 pm-10:51 am

1 stop14h 11m

Saint Thomas Island Cyril E King

Wed 1/22

11:46 am-10:50 pm

2 stops12h 04m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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.

Travel insights for flights from Massachusetts to Caribbean Islands

Get recent, data-driven insights about flights from Massachusetts to Caribbean Islands including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $335). 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 November 21, 2024.

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 November 21, 2024.

The most flights from USMA to zzEPX are scheduled on a Thursday (21 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 November 21, 2024.
See what other customers who have flown with Frontier, Spirit Airlines and JetBlue 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.
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,779 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,389 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 ($65), JetBlue ($68), and Spirit Airlines ($74).

  • 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 March is currently the most expensive (average of $335). 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$334FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$412FlexibilityNo cancel feeOn-time65%
DeltaCheapest$146Average$497FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$147Average$590FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$200Average$530FlexibilityNo cancel feeOn-time70%
AviancaCheapest$242Average$505FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$244Average$583FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$263Average$616FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$299Average$788FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$487Average$841FlexibilityNo cancel feeOn-time63%
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