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Caribbean Islands

$150+ Cheap flights from New Windsor (SWF) 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Stewart to Caribbean Islands

Keep the following information in mind while searching for Stewart to Caribbean Islands flight deals. Data was last updated September 17, 2025.

Round-trip from

$373
(Kiwi.com)

One-way from

$150
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$246
From New Windsor Stewart to Caribbean Islands
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One-way flight from New Windsor Stewart to Caribbean Islands
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Highest demand for flights based on searches. 6% potential increase in price ($20 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 September 2025
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Find flight deals from Stewart to Caribbean Islands

Cheapest flights from Stewart to Caribbean Islands
Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:11 pmSWF - MBJ
2 stops23h 06mMultiple Airlines
Sun 10/512:09 pmMBJ - SWF
1 stop21h 02mMultiple Airlines
Deal found 9/15$373
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:31 amSWF - MBJ
1 stop24h 29mMultiple Airlines
Thu 10/2312:09 pmMBJ - SWF
1 stop21h 32mMultiple Airlines
Deal found 9/15$374
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/1011:41 amSWF - STI
1 stop22h 57mMultiple Airlines
Thu 10/1611:43 amSTI - SWF
1 stop22h 58mMultiple Airlines
Deal found 9/16$379
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2811:43 amSWF - SDQ
2 stops28h 17mMultiple Airlines
Sun 10/53:54 pmSDQ - SWF
1 stop18h 17mMultiple Airlines
Deal found 9/15$384
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Mon 11/2410:57 amSWF - STI
1 stop29h 09mMultiple Airlines
Thu 12/116:18 pmSTI - SWF
1 stop18h 19mMultiple Airlines
Deal found 9/16$386
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2811:43 amSWF - MBJ
2 stops24h 22mMultiple Airlines
Sun 10/512:09 pmMBJ - SWF
1 stop21h 02mMultiple Airlines
Deal found 9/15$399
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Thu 10/3011:43 amSWF - PUJ
2 stops27h 17mMultiple Airlines
Thu 11/61:21 pmPUJ - SWF
1 stop22h 20mMultiple Airlines
Deal found 9/14$420
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/1011:41 amSWF - MBJ
1 stop26h 39mMultiple Airlines
Thu 10/1612:09 pmMBJ - SWF
1 stop21h 32mMultiple Airlines
Deal found 9/16$420
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/3111:31 amSWF - STI
1 stop23h 07mMultiple Airlines
Fri 11/76:18 pmSTI - SWF
2 stops43h 24mMultiple Airlines
Deal found 9/16$445
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:43 amSWF - BQN
1 stop14h 21mMultiple Airlines
Sat 10/182:59 amBQN - SWF
1 stop8h 04mMultiple Airlines
Deal found 9/15$447
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Mon 10/2011:01 amSWF - NAS
1 stop8h 14mMultiple Airlines
Thu 10/2311:30 amNAS - SWF
1 stop23h 11mMultiple Airlines
Deal found 9/16$456
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:11 pmSWF - NAS
1 stop7h 04mMultiple Airlines
Sun 10/54:00 pmNAS - SWF
1 stop18h 11mMultiple Airlines
Deal found 9/15$460

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart 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 September 17, 2025.
Use the filters below to find and compare flights from New Windsor to Caribbean Islands that are best for you.

Fly from

Stewart

Fly to

Caribbean Islands

Route

Depart

Return

Price

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/3

12:11 pm-10:17 am

2 stops23h 06m

Montego Bay Sangster Intl

Sun 10/5

12:09 pm-10:11 am

1 stop21h 02m

$373

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/17

11:31 am-11:00 am

1 stop24h 29m

Montego Bay Sangster Intl

Thu 10/23

12:09 pm-10:41 am

1 stop21h 32m

$373

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 10/10

11:41 am-10:38 am

1 stop22h 57m

Santiago de los Caballeros

Thu 10/16

11:43 am-10:41 am

1 stop22h 58m

$379

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Sun 9/28

11:43 am-4:00 pm

2 stops28h 17m

Santo Domingo Las Americas

Sun 10/5

3:54 pm-10:11 am

1 stop18h 17m

$384

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 11/24

10:57 am-5:06 pm

1 stop29h 09m

Santiago de los Caballeros

Thu 12/11

6:18 pm-11:37 am

1 stop18h 19m

$386

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Sun 9/28

11:43 am-11:05 am

2 stops24h 22m

Montego Bay Sangster Intl

Sun 10/5

12:09 pm-10:11 am

1 stop21h 02m

$399

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Thu 10/30

11:43 am-3:00 pm

2 stops27h 17m

Punta Cana

Thu 11/6

1:21 pm-10:41 am

1 stop22h 20m

$420

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 10/10

11:41 am-1:20 pm

1 stop26h 39m

Montego Bay Sangster Intl

Thu 10/16

12:09 pm-10:41 am

1 stop21h 32m

$420

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sun 1/11

11:48 am-10:59 pm

2 stops10h 11m

San Juan Luis Munoz Marin Intl

Thu 1/15

5:00 pm-10:19 am

1 stop18h 19m

$431

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 10/31

11:31 am-10:38 am

1 stop23h 07m

Santiago de los Caballeros

Fri 11/7

6:18 pm-12:42 pm

2 stops43h 24m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 results
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Best time to book a flight from Stewart to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Stewart 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 Windsor to Caribbean Islands

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

Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands in June is currently the most expensive (average of $339). 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 SWF to EPX?

Find hourly flight availability from Stewart 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 September 17, 2025.

When flying from New Windsor 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.

Related info for your journey

Find useful and relevant information for your journey from Stewart 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 Windsor to Caribbean Islands?

    For a flight from New Windsor to Caribbean Islands, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

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

    Most travelers choose New Windsor Stewart - San Juan Luis Munoz Marin Intl, New Windsor Stewart - Montego Bay Sangster Intl or New Windsor Stewart - Oranjestad Reina Beatrix when deciding on the best route from New Windsor to Caribbean Islands.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart 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 Windsor to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $254). Flying from New Windsor to Caribbean Islands in June is currently the most expensive (average of $339). 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 Stewart to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Stewart to Caribbean Islands

Discover the top airline that operate flights from Stewart 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$244Average$336FlexibilityNo cancel feeOn-time62%

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