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$128+ Cheap flights from New Windsor (SWF) to Caribbean

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Find flight deals from Stewart to Caribbean

Cheapest flights from Stewart to Caribbean
Explore the most affordable flight options available from Stewart to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This Mytrip deal was found by Cheapflights users on 10/25. 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 12/512:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 12/113:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 10/25$343
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/812:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 12/113:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 10/26$351
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/812:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Sun 12/143:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 10/26$353
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Thu 11/2011:43 amSWF - BQN
1 stop14h 20mMultiple Airlines
Sat 12/63:55 amBQN - SWF
1 stop8h 08mMultiple Airlines
Deal found 10/24$404
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 - MBJ
1 stop24h 29mMultiple Airlines
Sun 11/21:07 pmMBJ - SWF
1 stop22h 04mMultiple Airlines
Deal found 10/27$449
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/911:43 amSWF - SJU
1 stop14h 11mMultiple Airlines
Thu 11/133:37 pmSJU - SWF
1 stop19h 34mMultiple Airlines
Deal found 10/25$470
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/2612:17 pmSWF - STI
1 stop23h 05mMultiple Airlines
Sun 12/283:43 amSTI - SWF
1 stop8h 04mMultiple Airlines
Deal found 10/27$470
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/26:16 pmSWF - SJU
1 stop18h 06mMultiple Airlines
Sun 11/93:37 pmSJU - SWF
1 stop20h 34mMultiple Airlines
Deal found 10/26$471
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 - PUJ
1 stop27h 29mMultiple Airlines
Sun 11/24:25 pmPUJ - SWF
1 stop19h 46mMultiple Airlines
Deal found 10/27$472
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/2011:43 amSWF - SJU
1 stop8h 29mMultiple Airlines
Mon 11/2410:22 pmSJU - SWF
1 stop11h 31mMultiple Airlines
Deal found 10/25$477
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/196:56 pmSWF - AUA
1 stop19h 39mMultiple Airlines
Thu 12/254:40 pmAUA - SWF
1 stop19h 27mMultiple Airlines
Deal found 10/26$478
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/127:30 pmSWF - SJU
1 stop13h 25mMultiple Airlines
Thu 12/189:37 pmSJU - SWF
1 stop22h 44mMultiple Airlines
Deal found 10/26$481

Cheap flight deals from Stewart to Caribbean

Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated October 27, 2025.

Round-trip from

$290
(Kiwi.com)

One-way from

$128
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$218
From New Windsor Stewart to Caribbean
Search Deals
One-way flight from New Windsor Stewart to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Caribbean 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 October 27, 2025.
Use the filters below to find and compare flights from New Windsor to Caribbean that are best for you.

Fly from

Stewart

Fly to

Caribbean

Route

Depart

Return

Price

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 1/9

11:09 am-11:49 pm

1 stop11h 40m

San Juan Luis Munoz Marin Intl

Sun 1/18

5:00 pm-10:19 am

1 stop18h 19m

$290

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/5

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Thu 12/11

3:43 am-11:37 am

1 stop8h 54m

$343

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 12/8

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Thu 12/11

3:43 am-11:37 am

1 stop8h 54m

$351

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 12/8

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Sun 12/14

3:43 am-11:37 am

1 stop8h 54m

$353

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Fri 1/23

7:33 pm-9:55 am

1 stop13h 22m

San Juan Luis Munoz Marin Intl

Sat 1/24

3:55 am-11:08 am

1 stop8h 13m

$399

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Thu 11/20

11:43 am-3:03 am

1 stop14h 20m

Aguadilla Borinquen

Sat 12/6

3:55 am-11:03 am

1 stop8h 08m

$404

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Wed 11/26

12:17 pm-12:22 pm

1 stop23h 05m

Santiago de los Caballeros

Sun 12/28

3:43 am-10:47 am

1 stop8h 04m

$470

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Thu 11/20

11:43 am-9:12 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Mon 11/24

10:22 pm-8:53 am

1 stop11h 31m

$477

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Fri 12/19

6:56 pm-3:35 pm

1 stop19h 39m

Oranjestad Reina Beatrix

Thu 12/25

4:40 pm-11:07 am

1 stop19h 27m

$478

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 11/21

11:12 am-12:22 pm

1 stop24h 10m

Santiago de los Caballeros

Sat 11/29

1:17 pm-9:22 am

1 stop21h 05m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $79). Flying from New Windsor to Caribbean in August is currently the most expensive (average of $138). 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 CB?

Find hourly flight availability from Stewart to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 27, 2025.

One of the essential ways to save on airfare from New Windsor to Caribbean is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 47% on airfare.

Related info for your journey

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

    For a flight from New Windsor to Caribbean, 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?

    The most popular route from New Windsor to Caribbean is New Windsor Stewart - San Juan Luis Munoz Marin Intl. You may also consider New Windsor Stewart - Nassau Intl or New Windsor Stewart - Punta Cana.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Caribbean 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?

    Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean (average of $79). Flying from New Windsor to Caribbean in August is currently the most expensive (average of $138). 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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