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Stewart

$113+ Cheap flights from Caribbean Islands to New Windsor (SWF)

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Stewart

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

Round-trip from

$325
(Kiwi.com)

One-way from

$113
(Kiwi.com)
From Caribbean Islands to New Windsor Stewart
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One-way flight from Caribbean Islands to New Windsor Stewart
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Find flight deals from Caribbean Islands to Stewart

Cheapest flights from Caribbean Islands to Stewart
Explore the most affordable flight options available from Caribbean Islands to Stewart. 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.
Thu 10/93:54 pmSDQ - SWF
1 stop18h 57mMultiple Airlines
Fri 10/1711:31 amSWF - SDQ
1 stop27h 23mMultiple Airlines
Deal found 9/15$320
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.
Thu 10/163:54 pmSDQ - SWF
1 stop18h 47mMultiple Airlines
Fri 10/2411:31 amSWF - SDQ
1 stop27h 23mMultiple Airlines
Deal found 9/16$325
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.
Thu 11/66:55 pmSDQ - SWF
1 stop16h 46mMultiple Airlines
Mon 11/1012:01 pmSWF - SDQ
1 stop28h 49mMultiple Airlines
Deal found 9/16$328
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.
Thu 10/1611:51 amSJU - SWF
1 stop22h 50mMultiple Airlines
Thu 10/2311:43 amSWF - SJU
1 stop14h 01mMultiple Airlines
Deal found 9/16$423
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.
Thu 12/254:44 amSDQ - SWF
1 stop7h 23mMultiple Airlines
Fri 1/211:57 amSWF - SDQ
1 stop14h 09mMultiple Airlines
Deal found 9/16$557
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 12/184:44 amSDQ - SWF
1 stop14h 22mMultiple Airlines
Fri 1/211:57 amSWF - SDQ
1 stop14h 09mMultiple Airlines
Deal found 9/15$561
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.
Tue 11/256:18 pmSTI - SWF
1 stop18h 09mMultiple Airlines
Mon 12/15:49 pmSWF - STI
2 stops46h 17mMultiple Airlines
Deal found 9/15$568
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.
Wed 10/222:49 amSJU - SWF
1 stop8h 14mMultiple Airlines
Sun 10/2611:43 amSWF - SJU
1 stop14h 01mMultiple Airlines
Deal found 9/16$583
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 12/1911:30 amNAS - SWF
1 stop6h 36mMultiple Airlines
Mon 12/228:25 pmSWF - NAS
1 stop22h 50mMultiple Airlines
Deal found 9/16$584
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.
Thu 12/49:32 pmSJU - SWF
2 stops15h 12mMultiple Airlines
Sun 12/711:43 amSWF - SJU
1 stop10h 36mMultiple Airlines
Deal found 9/16$601
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.
Wed 10/292:49 amSJU - SWF
1 stop8h 14mMultiple Airlines
Mon 11/312:24 pmSWF - SJU
2 stops13h 20mMultiple Airlines
Deal found 9/16$602
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.
Sat 10/43:39 amSJU - SWF
1 stop7h 24mMultiple Airlines
Thu 10/911:43 amSWF - SJU
1 stop14h 01mMultiple Airlines
Deal found 9/15$606

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Stewart 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 Caribbean Islands to New Windsor that are best for you.

Fly from

Caribbean Islands

Fly to

Stewart

Route

Depart

Return

Price

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 10/9

3:54 pm-10:51 am

1 stop18h 57m

New Windsor Stewart

Fri 10/17

11:31 am-2:54 pm

1 stop27h 23m

$320

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 10/16

3:54 pm-10:41 am

1 stop18h 47m

New Windsor Stewart

Fri 10/24

11:31 am-2:54 pm

1 stop27h 23m

$325

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 11/6

6:55 pm-10:41 am

1 stop16h 46m

New Windsor Stewart

Mon 11/10

12:01 pm-5:50 pm

1 stop28h 49m

$328

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 10/16

11:51 am-10:41 am

1 stop22h 50m

New Windsor Stewart

Thu 10/23

11:43 am-1:44 am

1 stop14h 01m

$423

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 12/25

4:44 am-11:07 am

1 stop7h 23m

New Windsor Stewart

Fri 1/2

11:57 am-3:06 am

1 stop14h 09m

$557

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 12/18

4:44 am-6:06 pm

1 stop14h 22m

New Windsor Stewart

Fri 1/2

11:57 am-3:06 am

1 stop14h 09m

$561

Santiago de los CaballerosNew Windsor

STI - SWF

STISWF

Santiago de los Caballeros

Tue 11/25

6:18 pm-11:27 am

1 stop18h 09m

New Windsor Stewart

Mon 12/1

5:49 pm-5:06 pm

2 stops46h 17m

$568

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 10/22

2:49 am-11:03 am

1 stop8h 14m

New Windsor Stewart

Sun 10/26

11:43 am-1:44 am

1 stop14h 01m

$583

NassauNew Windsor

NAS - SWF

NASSWF

Nassau Intl

Fri 12/19

11:30 am-6:06 pm

1 stop6h 36m

New Windsor Stewart

Mon 12/22

8:25 pm-7:15 pm

1 stop22h 50m

$584

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 12/4

9:32 pm-11:44 am

2 stops15h 12m

New Windsor Stewart

Sun 12/7

11:43 am-11:19 pm

1 stop10h 36m

$601

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 46 results
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Best time to book a flight from Caribbean Islands to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Caribbean Islands to New Windsor (average of $109). Flying from Caribbean Islands to New Windsor in December is currently the most expensive (average of $202). 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 Caribbean Islands to Stewart. 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 into for flights to New Windsor from Caribbean Islands?

    New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly into when you book flights from Caribbean Islands to New Windsor.

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

    When deciding which route to take from Caribbean Islands to New Windsor consider San Juan Luis Munoz Marin Intl - New Windsor Stewart, Santo Domingo Las Americas - New Windsor Stewart or Santiago de los Caballeros - New Windsor Stewart as they are the most popular.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Caribbean Islands to New Windsor (average of $109). Flying from Caribbean Islands to New Windsor in December is currently the most expensive (average of $202). 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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