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Dominican Republic

$151+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PUJ
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
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 December 28, 2025.

This Mytrip deal was found by Cheapflights users on 12/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:45 pmSWF - PUJ
1 stop16h 24mMultiple Airlines
Sun 12/286:08 pmPUJ - SWF
1 stop17h 39mMultiple Airlines
Deal found 12/26$725
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Sat 12/278:45 pmSWF - SDQ
2 stops28h 05mMultiple Airlines
Sun 12/283:59 amSDQ - SWF
1 stop7h 48mMultiple Airlines
Deal found 12/26$778
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Tue 12/3011:43 amSWF - SDQ
1 stop14h 49mMultiple Airlines
Wed 1/147:25 pmSDQ - SWF
2 stops39h 54mMultiple Airlines
Deal found 12/26$890
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Sat 12/278:45 pmSWF - PUJ
1 stop21h 05mMultiple Airlines
Thu 1/16:08 pmPUJ - SWF
1 stop17h 59mMultiple Airlines
Deal found 12/25$951
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/266:41 pmSWF - STI
2 stops31h 01mMultiple Airlines
Sun 12/283:43 amSTI - SWF
1 stop8h 04mMultiple Airlines
Deal found 12/26$998
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Tue 12/3011:43 amSWF - SDQ
1 stop14h 49mMultiple Airlines
Thu 1/13:59 amSDQ - SWF
1 stop8h 08mMultiple Airlines
Deal found 12/28$1,031
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
Mon 12/2911:37 amSWF - SDQ
1 stop14h 17mMultiple Airlines
Thu 1/13:59 amSDQ - SWF
1 stop8h 08mMultiple Airlines
Deal found 12/25$1,061
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/2811:43 amSWF - SDQ
1 stop14h 49mMultiple Airlines
Wed 1/147:25 pmSDQ - SWF
2 stops39h 54mMultiple Airlines
Deal found 12/26$1,065
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Tue 12/3011:43 amSWF - SDQ
2 stops14h 11mMultiple Airlines
Sun 1/43:59 amSDQ - SWF
1 stop7h 48mMultiple Airlines
Deal found 12/26$1,150
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/2911:37 amSWF - STI
1 stop14h 05mMultiple Airlines
Thu 1/13:43 amSTI - SWF
1 stop8h 24mMultiple Airlines
Deal found 12/26$1,187
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/2911:37 amSWF - STI
1 stop14h 05mMultiple Airlines
Sun 1/43:43 amSTI - SWF
1 stop8h 04mMultiple Airlines
Deal found 12/26$1,276
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/2811:43 amSWF - SDQ
1 stop14h 49mMultiple Airlines
Sun 1/43:59 amSDQ - SWF
1 stop7h 48mMultiple Airlines
Deal found 12/26$1,339

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 December 28, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$338
(Kiwi.com)

One-way from

$151
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$578
Provider with most accurate pricing for New York (NYC)-Punta Cana flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Punta Cana flights.
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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. 4% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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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 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 December 28, 2025.
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

Mon 1/12

11:09 am-3:33 pm

1 stop27h 24m

Santiago de los Caballeros

Thu 1/15

4:40 pm-10:19 am

1 stop18h 39m

$338

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 1/9

11:09 am-3:33 pm

1 stop27h 24m

Santiago de los Caballeros

Sun 1/11

4:40 pm-10:19 am

1 stop18h 39m

$392

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 1/9

11:09 am-4:36 pm

1 stop28h 27m

Punta Cana

Sun 1/11

5:47 pm-10:19 am

1 stop17h 32m

$425

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 1/23

11:09 am-2:27 pm

1 stop26h 18m

Santo Domingo Las Americas

Fri 1/30

3:32 pm-5:59 pm

2 stops51h 27m

$460

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 2/12

11:42 am-3:35 pm

1 stop26h 53m

Santiago de los Caballeros

Sat 3/7

4:40 pm-8:19 am

1 stop16h 39m

$517

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 4/9

11:45 am-1:49 am

1 stop14h 04m

Santiago de los Caballeros

Sat 4/11

2:50 am-10:55 am

1 stop8h 05m

$594

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 3/1

11:52 am-3:35 pm

1 stop26h 43m

Santiago de los Caballeros

Sat 4/11

3:40 pm-10:55 am

1 stop19h 15m

$615

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

Sat 4/11

2:50 am-10:55 am

1 stop8h 05m

$651

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 2/13

11:04 am-8:25 pm

1 stop8h 21m

Punta Cana

Sat 2/21

6:50 pm-11:08 am

2 stops17h 18m

$764

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 2/9

11:09 am-4:36 pm

1 stop28h 27m

Punta Cana

Fri 2/27

9:15 pm-11:02 am

2 stops38h 47m

$981

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 36 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 $184). Flying from New Windsor to Dominican Republic in August is currently the most expensive (average of $256). 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 - Santiago de los Caballeros, New Windsor Stewart - Punta Cana 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 $184). Flying from New Windsor to Dominican Republic in August is currently the most expensive (average of $256). 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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