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Caribbean Islands

$76+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
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 December 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Fri 1/2310:52 amSJU - BOS
Nonstop4h 20mSpirit Airlines
Deal found 12/28$207
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sat 1/246:11 pmSJU - BOS
1 stop8h 02mMultiple Airlines
Deal found 12/28$215
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sun 1/113:55 amSJU - BOS
1 stop7h 51mMultiple Airlines
Deal found 12/29$219
This CheapOair deal was found by Cheapflights users on 12/30. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Fri 1/1610:52 amSJU - BOS
Nonstop4h 20mSpirit Airlines
Deal found 12/30$229
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sat 1/109:23 pmSJU - BOS
1 stop13h 48mMultiple Airlines
Deal found 12/29$240
This Kiwi.com deal was found by Cheapflights users on 12/29. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Wed 1/73:55 amSJU - BOS
1 stop7h 16mMultiple Airlines
Deal found 12/29$259
This CheapOair deal was found by Cheapflights users on 12/30. 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Sun 1/1110:52 amSJU - BOS
Nonstop4h 20mSpirit Airlines
Deal found 12/30$271
This Priceline deal was found by Cheapflights users on 12/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:10 pmBDL - SJU
Nonstop3h 49mMultiple Airlines
Wed 1/1412:59 pmSJU - BDL
Nonstop4h 15mMultiple Airlines
Deal found 12/29$298
This Delta deal was found by Cheapflights users on 12/28. 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.
Wed 12/3111:10 amBDL - SJU
1 stop11h 10mDelta
Wed 1/147:30 amSJU - BDL
1 stop7h 03mDelta
Deal found 12/28$310
This CheapOair deal was found by Cheapflights users on 12/29. 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.
Wed 12/3110:03 amBDL - SJU
Nonstop3h 56mFrontier
Wed 1/1412:59 pmSJU - BDL
Nonstop4h 15mFrontier
Deal found 12/29$313
This American Airlines deal was found by Cheapflights users on 12/28. 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.
Wed 12/3111:23 amBDL - SJU
1 stop7h 20mAmerican Airlines
Wed 1/146:00 amSJU - BDL
2 stops10h 47mAmerican Airlines
Deal found 12/28$320
This Priceline deal was found by Cheapflights users on 12/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:10 pmBDL - SJU
Nonstop3h 49mMultiple Airlines
Fri 1/93:55 amSJU - BDL
1 stop8h 48mMultiple Airlines
Deal found 12/30$331

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 December 31, 2025.

Round-trip from

$144
(Kiwi.com)

One-way from

$76
(Priceline)

Popular in

December

Cheapest in

January

Average price

$384
From Massachusetts to Caribbean Islands
Search Deals
One-way flight from Massachusetts to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 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 December 2025
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 December 31, 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

Wed 1/21

8:05 am-1:11 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:25 pm-5:45 pm

Nonstop4h 20m

$188

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 1/13

5:50 pm-10:55 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:15 am-9:25 am

Nonstop4h 10m

$188

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/17

10:27 am-3:30 pm

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Thu 2/26

12:15 pm-3:28 pm

Nonstop4h 13m

$195

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/31

12:45 pm-6:11 am

2 stops16h 26m

San Juan Luis Munoz Marin Intl

Wed 2/4

5:50 pm-11:49 pm

1 stop6h 59m

$197

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/3

6:00 am-4:50 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:55 pm-1:04 am

1 stop10h 09m

$197

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 4/1

9:30 pm-1:29 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Tue 4/7

5:01 am-9:10 am

Nonstop4h 09m

$202

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 2/1

6:00 am-4:50 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 3/31

7:00 am-6:27 pm

1 stop11h 27m

$204

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 3/24

8:05 am-12:04 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Tue 3/31

7:00 am-6:27 pm

1 stop11h 27m

$207

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 2/28

4:25 pm-6:11 am

2 stops12h 46m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:05 am-2:12 pm

1 stop7h 07m

$213

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Fri 1/23

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 1/27

2:00 pm-6:49 pm

1 stop5h 49m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

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 $88). 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 December 31, 2025.

It’s typically best to fly out from Massachusetts to Caribbean Islands in the afternoon. Doing so could potentially save you 24% 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 December 27, 2025.

Travelers seeking maximum savings on their Massachusetts to Caribbean Islands flight should consider departing on Sunday at noon 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 December 31, 2025.

The most flights from USMA to zzEPX are scheduled on a Tuesday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 05m. Fly via Delta, JetBlue, or Spirit Airlines to get the fastest option. The distance between Massachusetts and Caribbean Islands is about 1678 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 ($59).

  • 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 $88). 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

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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 December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$89Average$417FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$99Average$495FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$364FlexibilityNo cancel feeOn-time65%
Air CanadaCheapest$141Average$598FlexibilityNo cancel feeOn-time67%
DeltaCheapest$151Average$470FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$179Average$397FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$190Average$490FlexibilityNo cancel feeOn-time69%
ArajetCheapest$208Average$435FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$234Average$599FlexibilityNo cancel feeOn-time71%
AviancaCheapest$356Average$804FlexibilityNo cancel feeOn-time71%

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