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Caribbean Islands

$114+ Cheap flights from New Windsor (SWF) to Caribbean Islands

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 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap flight deals from Stewart to Caribbean Islands

Cheapest flights from Stewart to Caribbean Islands
Explore the most affordable flight options available from Stewart to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

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.
Mon 12/1512:27 pmSWF - AUA
1 stop26h 08mMultiple Airlines
Thu 12/184:40 pmAUA - SWF
1 stop26h 26mMultiple Airlines
Deal found 12/14$459
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.
Mon 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Sun 12/214:10 amSJU - SWF
1 stop16h 25mMultiple Airlines
Deal found 12/14$493
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.
Mon 12/1512:27 pmSWF - SJU
1 stop11h 18mMultiple Airlines
Thu 12/184:10 amSJU - SWF
1 stop14h 56mMultiple Airlines
Deal found 12/13$501
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.
Mon 12/157:30 pmSWF - PUJ
1 stop21h 30mMultiple Airlines
Thu 12/186:08 pmPUJ - SWF
1 stop24h 58mMultiple Airlines
Deal found 12/13$531
This Mytrip deal was found by Cheapflights users on 12/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:25 pmSWF - SJU
1 stop14h 33mMultiple Airlines
Thu 12/256:28 pmSJU - SWF
1 stop17h 39mMultiple Airlines
Deal found 12/15$548
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.
Mon 12/228:25 pmSWF - SJU
1 stop15h 04mMultiple Airlines
Sun 12/287:35 amSJU - SWF
1 stop28h 12mMultiple Airlines
Deal found 12/13$557
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.
Mon 12/228:25 pmSWF - PUJ
1 stop19h 25mMultiple Airlines
Thu 12/256:08 pmPUJ - SWF
1 stop17h 59mMultiple Airlines
Deal found 12/14$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.
Sat 12/209:45 amSWF - PUJ
1 stop27h 24mMultiple Airlines
Thu 12/256:08 pmPUJ - SWF
1 stop17h 59mMultiple Airlines
Deal found 12/13$579
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.
Mon 12/1512:24 pmSWF - BQN
2 stops13h 34mMultiple Airlines
Fri 12/196:42 pmBQN - SWF
1 stop15h 13mMultiple Airlines
Deal found 12/13$583
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.
Wed 12/245:34 pmSWF - PUJ
1 stop19h 35mMultiple Airlines
Sun 12/283:08 pmPUJ - SWF
2 stops20h 39mMultiple Airlines
Deal found 12/13$591
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 12/209:45 amSWF - SDQ
2 stops16h 09mMultiple Airlines
Thu 12/253:59 amSDQ - SWF
1 stop8h 08mMultiple Airlines
Deal found 12/14$620
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.
Mon 12/2212:24 pmSWF - SDQ
2 stops14h 08mMultiple Airlines
Thu 12/253:59 amSDQ - SWF
1 stop8h 08mMultiple Airlines
Deal found 12/13$621

Find flight deals from Stewart to Caribbean Islands

Keep the following information in mind while searching for Stewart to Caribbean Islands flight deals. Data was last updated December 15, 2025.

Round-trip from

$344
(Kiwi.com)

One-way from

$114
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$364
From New Windsor Stewart to Caribbean Islands
Search Deals
One-way flight from New Windsor Stewart to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($22 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
Search Deals

Cheapflights Fare Finder

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

Fly from

Stewart

Fly to

Caribbean Islands

Route

Depart

Return

Price

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 2/6

11:09 am-3:33 pm

1 stop27h 24m

Santiago de los Caballeros

Sat 2/14

4:40 pm-10:52 am

1 stop19h 12m

$344

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Mon 1/5

11:37 am-10:05 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Fri 1/9

6:00 am-6:43 pm

1 stop13h 43m

$388

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Thu 3/5

10:09 am-10:30 am

1 stop24h 21m

Nassau Intl

Sat 3/14

4:00 pm-11:39 am

1 stop19h 39m

$477

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 3/22

11:48 am-1:42 am

1 stop13h 54m

Aguadilla Borinquen

Wed 3/25

2:42 am-11:08 am

1 stop8h 26m

$478

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 2/27

11:03 am-8:25 pm

1 stop8h 22m

Punta Cana

Sun 3/1

11:35 am-10:13 am

1 stop23h 38m

$482

New WindsorSan Juan

SWF - SJU

SWFSJU

New Windsor Stewart

Sat 1/3

8:45 pm-8:58 am

1 stop11h 13m

San Juan Luis Munoz Marin Intl

Sat 1/10

9:19 pm-9:58 am

1 stop13h 39m

$513

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Sat 1/3

8:45 pm-2:09 pm

1 stop16h 24m

Punta Cana

Thu 1/8

5:47 pm-10:19 am

1 stop17h 32m

$516

New WindsorAguadilla

SWF - BQN

SWFBQN

New Windsor Stewart

Sun 3/22

11:48 am-1:42 am

1 stop13h 54m

Aguadilla Borinquen

Sat 3/28

2:42 am-11:08 am

1 stop8h 26m

$528

New WindsorNassau

SWF - NAS

SWFNAS

New Windsor Stewart

Sun 5/24

10:28 am-7:15 pm

1 stop8h 47m

Nassau Intl

Sat 5/30

4:00 pm-9:38 am

1 stop17h 38m

$528

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 2/13

11:04 am-8:25 pm

1 stop8h 21m

Punta Cana

Sun 2/15

11:35 am-10:14 am

1 stop23h 39m

$542

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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

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

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

Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $79). Flying from New Windsor to Caribbean Islands 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 EPX?

Find hourly flight availability from Stewart to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

One of the essential ways to save on airfare from New Windsor to Caribbean Islands 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 Islands. 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 Islands?

    For a flight from New Windsor to Caribbean Islands, 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 Islands?

    Most travelers choose New Windsor Stewart - San Juan Luis Munoz Marin Intl, New Windsor Stewart - Punta Cana or New Windsor Stewart - Aguadilla Borinquen when deciding on the best route from New Windsor to Caribbean Islands.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from New Windsor to Caribbean Islands (average of $79). Flying from New Windsor to Caribbean Islands 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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See prices for flight routes from nearby airports that may be better suited for you.
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