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Caribbean Islands

$655+ Cheap flights from New Bedford (EWB) 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
EWB — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from New Bedford to Caribbean Islands

One-way flights from New Bedford to Caribbean Islands
Search for one-way flight options from New Bedford to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated December 12, 2025.

This KAYAK deal was found by Cheapflights users on 12/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:00 amEWB - STI
2 stops18h 15mMultiple Airlines
Deal found 12/10$655
This KAYAK deal was found by Cheapflights users on 12/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/127:00 amEWB - SJU
2 stops17h 50mMultiple Airlines
Deal found 12/10$947
This KAYAK deal was found by Cheapflights users on 12/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:00 amEWB - SDQ
2 stops16h 45mMultiple Airlines
Deal found 12/10$948
This KAYAK deal was found by Cheapflights users on 12/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:00 amEWB - SDQ
2 stops9h 14mMultiple Airlines
Deal found 12/10$1,079
This KAYAK deal was found by Cheapflights users on 12/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/137:00 amEWB - SJU
2 stops42h 52mMultiple Airlines
Deal found 12/11$1,079
This KAYAK deal was found by Cheapflights users on 12/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:00 amEWB - SDQ
2 stops33h 14mMultiple Airlines
Deal found 12/10$1,080
This KAYAK deal was found by Cheapflights users on 12/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:00 amEWB - SDQ
2 stops20h 41mMultiple Airlines
Deal found 12/10$1,081

Find flight deals from New Bedford to Caribbean Islands

Keep the following information in mind while searching for New Bedford to Caribbean Islands flight deals. Data was last updated December 12, 2025.

Popular in

December

Cheapest in

January

Average price

$388
Highest demand for flights based on searches. 7% potential increase in price ($25 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 New Bedford 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 12, 2025.
Use the filters below to find and compare flights from New Bedford to Caribbean Islands that are best for you.

Fly from

New Bedford

Fly to

Caribbean Islands

Route

Depart

Return

Price

New BedfordSantiago de los Caballeros

EWB - STI

EWBSTI

New Bedford Regional

Tue 3/31

7:00 am-1:15 am

2 stops18h 15m

$655

New BedfordSan Juan

EWB - SJU

EWBSJU

New Bedford Regional

Thu 2/12

7:00 am-1:50 am

2 stops17h 50m

$947

New BedfordSanto Domingo

EWB - SDQ

EWBSDQ

New Bedford Regional

Wed 12/17

7:00 am-12:45 am

2 stops16h 45m

$948

New BedfordSanto Domingo

EWB - SDQ

EWBSDQ

New Bedford Regional

Fri 12/19

7:00 am-5:14 pm

2 stops9h 14m

$1,079

New BedfordSan Juan

EWB - SJU

EWBSJU

New Bedford Regional

Fri 2/13

7:00 am-2:52 am

2 stops42h 52m

$1,079

New BedfordSanto Domingo

EWB - SDQ

EWBSDQ

New Bedford Regional

Thu 12/18

7:00 am-5:14 pm

2 stops33h 14m

$1,080

New BedfordSanto Domingo

EWB - SDQ

EWBSDQ

New Bedford Regional

Mon 12/22

7:00 am-4:41 am

2 stops20h 41m

$1,081

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Best time to book a flight from New Bedford to Caribbean Islands

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

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

Currently, January is the cheapest month in which you can book a flight from New Bedford to Caribbean Islands (average of $88). Flying from New Bedford 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.

Related info for your journey

Find useful and relevant information for your journey from New Bedford 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 airport do you fly from for flights from New Bedford to Caribbean Islands?

    Located just 3.0 mi from the city center, New Bedford Regional (EWB) is the airport most travelers will use when flying to Caribbean Islands from New Bedford.

  • What are the most popular routes from New Bedford to Caribbean Islands?

    Most travelers choose New Bedford Regional - Bridgetown Grantley Adams Intl, New Bedford Regional - Kingston Norman Manley or New Bedford Regional - Ponce Mercedita when deciding on the best route from New Bedford to Caribbean Islands.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from New Bedford 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 New Bedford to Caribbean Islands?

    Currently, January is the cheapest month in which you can book a flight from New Bedford to Caribbean Islands (average of $88). Flying from New Bedford 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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