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Stewart

$142+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
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 July 25, 2025.

Round-trip from

$266
(Mytrip)

One-way from

$142
(Mytrip)
From Caribbean Islands to New Windsor Stewart
Search Deals
One-way flight from Caribbean Islands to New Windsor Stewart
Search Deals

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 July 25, 2025.

This Mytrip deal was found by Cheapflights users on 7/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/212:11 amSJU - SWF
2 stops14h 35mMultiple Airlines
Mon 8/255:36 pmSWF - SJU
2 stops23h 06mMultiple Airlines
Deal found 7/23$266
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/1510:20 amSTI - SWF
1 stop8h 27mMultiple Airlines
Mon 8/187:37 pmSWF - STI
1 stop13h 38mMultiple Airlines
Deal found 7/22$368
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/110:55 amSDQ - SWF
1 stop8h 11mMultiple Airlines
Fri 8/291:55 pmSWF - SDQ
1 stop26h 05mMultiple Airlines
Deal found 7/24$368
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 7/313:25 pmPUJ - SWF
1 stop27h 41mMultiple Airlines
Sat 8/97:29 pmSWF - PUJ
1 stop13h 25mMultiple Airlines
Deal found 7/22$380
This Mytrip deal was found by Cheapflights users on 7/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/17:55 amKIN - SWF
1 stop10h 11mMultiple Airlines
Fri 8/87:56 pmSWF - KIN
1 stop12h 51mMultiple Airlines
Deal found 7/23$427
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 7/244:00 pmNAS - SWF
1 stop27h 06mMultiple Airlines
Fri 8/225:36 pmSWF - NAS
1 stop16h 54mMultiple Airlines
Deal found 7/22$569
This Mytrip deal was found by Cheapflights users on 7/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/110:10 amPOS - SWF
1 stop8h 56mMultiple Airlines
Sat 8/95:51 pmSWF - POS
2 stops26h 09mMultiple Airlines
Deal found 7/23$968

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 July 25, 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

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 8/21

2:11 am-4:46 pm

2 stops14h 35m

New Windsor Stewart

Mon 8/25

5:36 pm-4:42 pm

2 stops23h 06m

$266

Santiago de los CaballerosNew Windsor

STI - SWF

STISWF

Santiago de los Caballeros

Fri 8/15

10:20 am-6:47 pm

1 stop8h 27m

New Windsor Stewart

Mon 8/18

7:37 pm-9:15 am

1 stop13h 38m

$368

Punta CanaNew Windsor

PUJ - SWF

PUJSWF

Punta Cana

Thu 7/31

3:25 pm-7:06 pm

1 stop27h 41m

New Windsor Stewart

Sat 8/9

7:29 pm-8:54 am

1 stop13h 25m

$380

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Thu 8/7

11:50 am-7:12 pm

1 stop7h 22m

New Windsor Stewart

Fri 8/29

1:55 pm-4:00 pm

1 stop26h 05m

$418

KingstonNew Windsor

KIN - SWF

KINSWF

Kingston Norman Manley

Fri 8/1

7:55 am-7:06 pm

1 stop10h 11m

New Windsor Stewart

Fri 8/8

7:56 pm-7:47 am

1 stop12h 51m

$427

NassauNew Windsor

NAS - SWF

NASSWF

Nassau Intl

Mon 11/24

7:15 am-5:09 pm

1 stop9h 54m

New Windsor Stewart

Fri 11/28

12:24 pm-9:00 pm

2 stops8h 36m

$752

Port of SpainNew Windsor

POS - SWF

POSSWF

Port of Spain Piarco Intl

Fri 8/1

10:10 am-7:06 pm

1 stop8h 56m

New Windsor Stewart

Sat 8/9

5:51 pm-8:00 pm

2 stops26h 09m

$968

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 8/28

8:00 am-1:05 pm

2 stops29h 05m

$142

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Fri 8/1

10:55 am-7:06 pm

1 stop8h 11m

$176

Punta CanaNew Windsor

PUJ - SWF

PUJSWF

Punta Cana

Thu 8/14

4:05 pm-6:47 pm

1 stop26h 42m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 16 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 August is currently the most expensive (average of $216). 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 Nassau Intl - 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 August is currently the most expensive (average of $216). 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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