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$129+ 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
Jan 9 — Jan 161
Fri 1/9
Fri 1/16
1 adult, Economy
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Cheap 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 December 10, 2025.

This Mytrip deal was found by Cheapflights users on 12/8. 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.
Mon 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Thu 12/184:10 amSJU - SWF
1 stop14h 56mMultiple Airlines
Deal found 12/8$323
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/1512:27 pmSWF - AUA
1 stop26h 08mMultiple Airlines
Thu 12/184:40 pmAUA - SWF
1 stop26h 26mMultiple Airlines
Deal found 12/8$340
This Mytrip deal was found by Cheapflights users on 12/8. 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 12/1212:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 12/8$343
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Thu 12/186:28 pmSJU - SWF
1 stop24h 38mMultiple Airlines
Deal found 12/9$355
This Mytrip deal was found by Cheapflights users on 12/7. 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.
Mon 12/812:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 12/7$362
This Mytrip deal was found by Cheapflights users on 12/9. 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 12/1212:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Thu 12/184:10 amSJU - SWF
1 stop14h 56mMultiple Airlines
Deal found 12/9$366
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/1111:43 amSWF - SJU
1 stop11h 33mMultiple Airlines
Sun 12/144:10 amSJU - SWF
1 stop8h 27mMultiple Airlines
Deal found 12/7$412
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/1212:27 pmSWF - PUJ
1 stop27h 23mMultiple Airlines
Sun 12/146:08 pmPUJ - SWF
1 stop18h 29mMultiple Airlines
Deal found 12/8$429
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/1411:43 amSWF - BQN
1 stop14h 15mMultiple Airlines
Sat 1/103:43 amBQN - SWF
1 stop8h 50mMultiple Airlines
Deal found 12/10$446
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/1512:27 pmSWF - PUJ
2 stops21h 09mMultiple Airlines
Thu 12/186:08 pmPUJ - SWF
1 stop24h 58mMultiple Airlines
Deal found 12/8$452
This Mytrip deal was found by Cheapflights users on 12/9. 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.
Mon 12/1512:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 12/183:43 amSTI - SWF
1 stop15h 23mMultiple Airlines
Deal found 12/9$452
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/1411:43 amSWF - BQN
1 stop14h 15mMultiple Airlines
Wed 1/73:53 amBQN - SWF
1 stop8h 40mMultiple Airlines
Deal found 12/10$471

Find flight deals from Stewart to Caribbean

Keep the following information in mind while searching for Stewart to Caribbean flight deals. Data was last updated December 10, 2025.

Round-trip from

$303
(Mytrip)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$365
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. 8% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 10, 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 WindsorSimpson Bay

SWF - SXM

SWFSXM

New Windsor Stewart

Fri 1/23

11:09 am-2:10 pm

1 stop26h 01m

Simpson Bay Princess Juliana

Sun 2/1

3:15 pm-10:19 am

1 stop20h 04m

$303

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/15

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/18

4:10 am-6:06 pm

1 stop14h 56m

$323

New WindsorOranjestad

SWF - AUA

SWFAUA

New Windsor Stewart

Fri 2/6

11:09 am-3:35 pm

1 stop27h 26m

Oranjestad Reina Beatrix

Sat 2/14

4:41 pm-10:52 am

1 stop19h 11m

$333

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Thu 1/22

12:13 pm-3:35 pm

2 stops26h 22m

Santo Domingo Las Americas

Thu 1/29

4:40 pm-10:19 am

1 stop18h 39m

$387

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 12/15

12:27 pm-12:45 am

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Thu 12/18

11:38 am-6:06 pm

2 stops31h 28m

$391

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Thu 1/22

12:13 pm-4:36 pm

2 stops27h 23m

Punta Cana

Thu 1/29

5:47 pm-10:19 am

1 stop17h 32m

$391

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 1/5

11:37 am-2:42 am

1 stop14h 05m

Santiago de los Caballeros

Sat 1/31

4:40 pm-9:58 am

2 stops18h 18m

$418

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 1/8

6:49 pm-3:33 pm

2 stops43h 44m

Santiago de los Caballeros

Thu 1/15

4:40 pm-10:19 am

1 stop18h 39m

$438

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Thu 1/1

11:43 am-4:50 pm

2 stops28h 07m

Punta Cana

Thu 1/22

5:47 pm-10:19 am

1 stop17h 32m

$465

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 5/1

11:40 am-8:25 pm

1 stop8h 45m

Punta Cana

Fri 5/8

1:10 pm-11:25 am

2 stops22h 15m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

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 December 10, 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 in the afternoon could potentially save you up to 53% 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 - Providenciales 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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