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Caribbean Islands

$68+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
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Cheap 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 February 16, 2026.

This Super.com deal was found by Cheapflights users on 2/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/110:04 am
BOS
-
SJU
Nonstop3h 56m
Frontier
Thu 3/56:00 am
SJU
-
BOS
Nonstop4h 19m
Frontier
Deal found 2/12$143
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Tue 2/245:27 am
BOS
-
SJU
1 stop9h 04m
Multiple Airlines
Thu 2/266:00 am
SJU
-
BOS
Nonstop4h 19m
Multiple Airlines
Deal found 2/12$145
This Cheapflightsfares deal was found by Cheapflights users on 2/16. 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 2/238:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Tue 3/311:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/16$146
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/18:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Fri 3/611:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/15$147
This Travelocity deal was found by Cheapflights users on 2/12. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Tue 3/1010:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/12$148
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 2/225:27 am
BOS
-
SJU
1 stop9h 04m
Spirit Airlines
Thu 2/263:30 pm
SJU
-
BOS
Nonstop4h 26m
Spirit Airlines
Deal found 2/12$149
This Orbitz deal was found by Cheapflights users on 2/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Thu 3/53:30 pm
SJU
-
BOS
Nonstop4h 26m
Spirit Airlines
Deal found 2/15$150
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Tue 2/243:00 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Fri 3/611:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/16$151
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/210:04 am
BOS
-
SJU
Nonstop3h 56m
Multiple Airlines
Tue 3/1010:22 am
SJU
-
BOS
Nonstop4h 21m
Multiple Airlines
Deal found 2/14$152
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 3/13:00 pm
BOS
-
SJU
Nonstop4h 06m
Spirit Airlines
Wed 3/1110:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/13$153
This Orbitz deal was found by Cheapflights users on 2/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:01 pm
BOS
-
SJU
Nonstop4h 07m
Spirit Airlines
Wed 3/411:22 am
SJU
-
BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/13$154
This eDestinos deal was found by Cheapflights users on 2/12. 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 5/148:08 pm
BDL
-
SJU
1 stop17h 58m
Frontier
Mon 5/1811:59 pm
SJU
-
BDL
Nonstop4h 06m
Frontier
Deal found 2/12$187

Find 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 February 16, 2026.

Round-trip from

$143
(Super.com)

One-way from

$68
(eDestinos)

Popular in

December

Cheapest in

March

Average price

$299
From Massachusetts to Caribbean Islands
Search Deals
One-way flight from Massachusetts to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 16, 2026.
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

Mon 3/2

4:22 pm-10:17 am

1 stop16h 55m

San Juan Luis Munoz Marin Intl

Thu 3/5

4:36 pm-11:44 pm

1 stop8h 08m

$236

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 3/28

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Wed 4/1

2:45 pm-7:04 pm

Nonstop4h 19m

$241

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/24

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Tue 3/31

2:45 pm-7:04 pm

Nonstop4h 19m

$241

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 4/2

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Wed 4/8

2:45 pm-7:04 pm

Nonstop4h 19m

$241

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 3/8

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Mon 3/16

2:45 pm-7:04 pm

Nonstop4h 19m

$241

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/31

8:40 am-12:43 pm

Nonstop4h 03m

Saint Thomas Island Cyril E King

Tue 4/7

2:45 pm-7:04 pm

Nonstop4h 19m

$241

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 3/1

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 3/4

2:32 pm-5:53 pm

Nonstop4h 21m

$241

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 2/26

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 3/4

2:32 pm-5:53 pm

Nonstop4h 21m

$241

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/3

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 3/10

2:45 pm-7:04 pm

Nonstop4h 19m

$241

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/3

9:40 am-10:22 pm

2 stops11h 42m

San Juan Luis Munoz Marin Intl

Thu 3/5

2:05 am-7:45 am

1 stop6h 40m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

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, January is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $93). Flying from Massachusetts to Caribbean Islands in November is currently the most expensive (average of $177). 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 February 16, 2026.

It’s typically best to fly out from Massachusetts to Caribbean Islands in the afternoon. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Massachusetts to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Caribbean Islands. Price data was last updated on February 7, 2026.

Travelers seeking maximum savings on their Massachusetts to Caribbean Islands flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 16, 2026.

The most flights from USMA to zzEPX are scheduled on a Sunday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (16 on average).

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.

  • How long is the flight from Massachusetts to Caribbean Islands?

    There are many flights that can get you from Massachusetts to Caribbean Islands in 4h 03m. Fly via Spirit Airlines, Delta, or United Airlines to get the fastest option. The distance between Massachusetts and Caribbean Islands is about 1697 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 ($44), Delta ($54), and Spirit Airlines ($61).

  • 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, January is the cheapest month in which you can book a flight from Massachusetts to Caribbean Islands (average of $93). Flying from Massachusetts to Caribbean Islands in November is currently the most expensive (average of $177). 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

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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 9 airlines flying from Massachusetts to Caribbean Islands

Discover the top 9 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 February 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$400FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$86Average$347FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$130Average$614FlexibilityNo cancel feeOn-time67%
DeltaCheapest$137Average$447FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$141Average$496FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$166Average$471FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$179Average$366FlexibilityNo cancel feeOn-time70%
ArajetCheapest$187Average$380FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$234Average$579FlexibilityNo cancel feeOn-time71%

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