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Dominican Republic

$176+ Cheap flights from New Windsor (SWF) to the Dominican Republic

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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PUJ
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
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Cheap flight deals from Stewart to Dominican Republic

Cheapest flights from Stewart to Dominican Republic
Explore the most affordable flight options available from Stewart to Dominican Republic. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/1910:29 am
SWF
-
STI
1 stop15h 20m
Multiple Airlines
Wed 4/82:46 am
STI
-
SWF
1 stop8h 09m
Multiple Airlines
Deal found 2/16$430
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/111:52 am
SWF
-
PUJ
1 stop27h 44m
Multiple Airlines
Sun 3/2911:35 am
PUJ
-
SWF
1 stop21h 22m
Multiple Airlines
Deal found 2/14$432
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/210:29 am
SWF
-
SDQ
1 stop15h 09m
Multiple Airlines
Wed 4/82:20 pm
SDQ
-
SWF
1 stop20h 35m
Multiple Airlines
Deal found 2/17$455
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/310:00 am
SWF
-
PUJ
1 stop10h 25m
Multiple Airlines
Wed 4/84:25 pm
PUJ
-
SWF
2 stops18h 30m
Multiple Airlines
Deal found 2/17$461
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/210:29 am
SWF
-
STI
1 stop15h 20m
Multiple Airlines
Wed 4/82:46 am
STI
-
SWF
1 stop8h 09m
Multiple Airlines
Deal found 2/15$477
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Thu 3/1210:09 am
SWF
-
STI
1 stop15h 40m
Multiple Airlines
Sat 3/142:46 am
STI
-
SWF
1 stop8h 53m
Multiple Airlines
Deal found 2/14$483
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 3/2610:29 am
SWF
-
SDQ
1 stop15h 09m
Multiple Airlines
Wed 4/82:20 pm
SDQ
-
SWF
1 stop20h 35m
Multiple Airlines
Deal found 2/17$497
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Thu 2/2611:52 am
SWF
-
SDQ
1 stop25h 28m
Multiple Airlines
Sun 3/110:46 am
SDQ
-
SWF
1 stop24h 27m
Multiple Airlines
Deal found 2/14$510
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 4/210:29 am
SWF
-
SDQ
2 stops40h 11m
Multiple Airlines
Wed 4/82:52 am
SDQ
-
SWF
1 stop8h 03m
Multiple Airlines
Deal found 2/16$553
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
Fri 2/2711:03 am
SWF
-
PUJ
1 stop8h 22m
Multiple Airlines
Sun 3/111:35 am
PUJ
-
SWF
1 stop23h 38m
Multiple Airlines
Deal found 2/14$575
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 4/510:29 am
SWF
-
SDQ
1 stop26h 46m
Multiple Airlines
Sat 4/112:20 pm
SDQ
-
SWF
1 stop20h 35m
Multiple Airlines
Deal found 2/16$593
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 4/510:29 am
SWF
-
STI
1 stop15h 20m
Multiple Airlines
Sat 4/113:28 pm
STI
-
SWF
1 stop19h 27m
Multiple Airlines
Deal found 2/14$606

Find flight deals from Stewart to Dominican Republic

Keep the following information in mind while searching for Stewart to Dominican Republic flight deals. Data was last updated February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$430
(Kiwi.com)

One-way from

$176
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$484
Provider with most accurate pricing for New York (NYC)-Punta Cana flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Punta Cana flights.
Search Deals
From New Windsor Stewart to Dominican Republic
Search Deals
One-way flight from New Windsor Stewart to Dominican Republic
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Dominican Republic 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 February 18, 2026.
Use the filters below to find and compare flights from New Windsor to the Dominican Republic that are best for you.

Fly from

Stewart

Fly to

Dominican Republic

Route

Depart

Return

Price

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 3/19

10:29 am-1:49 am

1 stop15h 20m

Santiago de los Caballeros

Wed 4/8

2:46 am-10:55 am

1 stop8h 09m

$430

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Sun 3/1

11:52 am-4:36 pm

1 stop27h 44m

Punta Cana

Sun 3/29

11:35 am-8:57 am

1 stop21h 22m

$432

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Thu 4/2

10:29 am-1:38 am

1 stop15h 09m

Santo Domingo Las Americas

Wed 4/8

2:20 pm-10:55 am

1 stop20h 35m

$455

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 4/3

10:00 am-8:25 pm

1 stop10h 25m

Punta Cana

Wed 4/8

4:25 pm-10:55 am

2 stops18h 30m

$461

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 4/2

10:29 am-1:49 am

1 stop15h 20m

Santiago de los Caballeros

Wed 4/8

2:46 am-10:55 am

1 stop8h 09m

$477

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 3/12

10:09 am-1:49 am

1 stop15h 40m

Santiago de los Caballeros

Sat 3/14

2:46 am-11:39 am

1 stop8h 53m

$483

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Thu 4/2

10:29 am-1:38 am

1 stop15h 09m

Santo Domingo Las Americas

Wed 4/8

2:52 am-10:55 am

1 stop8h 03m

$497

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Thu 3/26

10:29 am-1:38 am

1 stop15h 09m

Santo Domingo Las Americas

Wed 4/8

2:20 pm-10:55 am

1 stop20h 35m

$497

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 4/3

10:00 am-8:25 pm

1 stop10h 25m

Punta Cana

Sun 4/12

11:35 am-10:50 am

1 stop23h 15m

$547

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

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 52 results
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Best time to book a flight from Stewart to Dominican Republic

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

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Dominican Republic (average of $142). Flying from New Windsor to Dominican Republic in August is currently the most expensive (average of $238). 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 Stewart to Dominican Republic. 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 Dominican Republic?

    For a flight from New Windsor to Dominican Republic, 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 Dominican Republic?

    When deciding which route to take from New Windsor to Dominican Republic consider New Windsor Stewart - Punta Cana, New Windsor Stewart - Santiago de los Caballeros or New Windsor Stewart - Santo Domingo Las Americas as they are the most popular.

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

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

  • How can I find direct flights from Stewart to Dominican Republic?

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

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

    Yes. Cheapflights offers flight deals from Stewart to Dominican Republic 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 Dominican Republic?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Dominican Republic (average of $142). Flying from New Windsor to Dominican Republic in August is currently the most expensive (average of $238). 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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Alternative routes for Stewart to Dominican Republic

See prices for flight routes from nearby airports that may be better suited for you.
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