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Stewart

$125+ 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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — SWF
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Mytrip deal was found by Cheapflights users on 12/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:43 amSTI - SWF
1 stop8h 24mMultiple Airlines
Mon 1/511:37 amSWF - STI
1 stop14h 05mMultiple Airlines
Deal found 12/14$327
This Mytrip deal was found by Cheapflights users on 12/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:59 amSDQ - SWF
1 stop7h 48mMultiple Airlines
Mon 1/511:37 amSWF - SDQ
1 stop14h 17mMultiple Airlines
Deal found 12/14$431
This eDestinos deal was found by Cheapflights users on 12/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:00 amSJU - SWF
1 stop13h 06mMultiple Airlines
Mon 12/228:25 pmSWF - SJU
1 stop15h 04mMultiple Airlines
Deal found 12/13$487
This Mytrip deal was found by Cheapflights users on 12/12. 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.
Sun 12/213:43 amSTI - SWF
1 stop16h 52mMultiple Airlines
Fri 1/211:57 amSWF - STI
1 stop13h 45mMultiple Airlines
Deal found 12/12$490
This Mytrip deal was found by Cheapflights users on 12/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:28 pmSJU - SWF
1 stop17h 19mMultiple Airlines
Fri 1/211:57 amSWF - SJU
1 stop9h 08mMultiple Airlines
Deal found 12/14$508
This Mytrip deal was found by Cheapflights users on 12/13. 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.
Sun 12/282:59 amSJU - SWF
1 stop10h 03mMultiple Airlines
Fri 1/211:57 amSWF - SJU
1 stop9h 08mMultiple Airlines
Deal found 12/13$562
This Mytrip deal was found by Cheapflights users on 12/12. 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 12/256:28 pmSJU - SWF
1 stop17h 39mMultiple Airlines
Mon 12/2911:37 amSWF - SJU
1 stop9h 28mMultiple Airlines
Deal found 12/12$566
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/1910:17 pmSJU - SWF
1 stop11h 38mMultiple Airlines
Tue 12/236:28 pmSWF - SJU
2 stops26h 37mMultiple Airlines
Deal found 12/13$621
This Mytrip deal was found by Cheapflights users on 12/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Mon 12/228:25 pmSWF - SJU
1 stop14h 33mMultiple Airlines
Deal found 12/14$637
This Kiwi.com deal was found by Cheapflights users on 12/12. 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 12/243:55 amSJU - SWF
1 stop8h 08mMultiple Airlines
Thu 1/111:43 amSWF - SJU
1 stop13h 29mMultiple Airlines
Deal found 12/12$667
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Sat 12/278:20 amSDQ - SWF
1 stop12h 35mMultiple Airlines
Mon 1/1911:09 amSWF - SDQ
2 stops14h 08mMultiple Airlines
Deal found 12/14$696
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Sun 12/143:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Mon 12/228:25 pmSWF - STI
1 stop29h 17mMultiple Airlines
Deal found 12/14$1,022

Find 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 December 15, 2025.

Round-trip from

$327
(Mytrip)

One-way from

$134
(Kiwi.com)
From Caribbean Islands to New Windsor Stewart
Search Deals
One-way flight from Caribbean Islands to New Windsor Stewart
Search Deals

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 December 15, 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

Santiago de los CaballerosNew Windsor

STI - SWF

STISWF

Santiago de los Caballeros

Thu 12/25

3:43 am-11:07 am

1 stop8h 24m

New Windsor Stewart

Mon 1/5

11:37 am-2:42 am

1 stop14h 05m

$327

Santo DomingoNew Windsor

SDQ - SWF

SDQSWF

Santo Domingo Las Americas

Sun 12/28

3:59 am-10:47 am

1 stop7h 48m

New Windsor Stewart

Mon 1/5

11:37 am-2:54 am

1 stop14h 17m

$431

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/18

7:54 pm-9:39 am

1 stop13h 45m

New Windsor Stewart

Sun 3/22

11:48 am-8:43 am

1 stop20h 55m

$478

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 1/1

6:28 pm-11:07 am

1 stop17h 39m

New Windsor Stewart

Mon 1/5

11:37 am-10:05 pm

1 stop9h 28m

$488

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sun 12/28

6:28 pm-10:47 am

1 stop17h 19m

New Windsor Stewart

Fri 1/2

11:57 am-10:05 pm

1 stop9h 08m

$508

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 2/5

8:05 pm-11:31 am

2 stops16h 26m

New Windsor Stewart

Sun 2/8

11:48 am-11:33 pm

1 stop10h 45m

$528

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Wed 3/4

3:53 am-11:08 am

1 stop8h 15m

New Windsor Stewart

Sun 3/8

11:48 am-10:45 pm

1 stop10h 57m

$538

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Sun 12/28

2:59 am-12:02 pm

1 stop10h 03m

New Windsor Stewart

Fri 1/2

11:57 am-10:05 pm

1 stop9h 08m

$562

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 1/15

8:05 pm-11:31 am

2 stops16h 26m

New Windsor Stewart

Sun 1/18

12:13 pm-3:03 am

1 stop13h 50m

$564

San JuanNew Windsor

SJU - SWF

SJUSWF

San Juan Luis Munoz Marin Intl

Thu 12/25

6:28 pm-11:07 am

1 stop17h 39m

New Windsor Stewart

Mon 12/29

11:37 am-10:05 pm

1 stop9h 28m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 44 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, February is the cheapest month in which you can book a flight from Caribbean Islands to New Windsor (average of $75). Flying from Caribbean Islands to New Windsor in August is currently the most expensive (average of $118). 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, Simpson Bay Princess Juliana - New Windsor Stewart or Santo Domingo Las Americas - 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, February is the cheapest month in which you can book a flight from Caribbean Islands to New Windsor (average of $75). Flying from Caribbean Islands to New Windsor in August is currently the most expensive (average of $118). 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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