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Dominican Republic

$156+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PUJ
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap 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 November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$333
(Mytrip)

One-way from

$156
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$486
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
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One-way flight from New Windsor Stewart to Dominican Republic
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Highest demand for flights based on searches. 6% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 6, 2025.

This Mytrip deal was found by Cheapflights users on 11/5. 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 11/5$333
This Mytrip deal was found by Cheapflights users on 11/6. 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
Sun 12/143:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 11/6$360
This Mytrip deal was found by Cheapflights users on 11/5. 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 11/1712:01 pmSWF - PUJ
2 stops23h 44mMultiple Airlines
Sun 11/233:11 pmPUJ - SWF
2 stops19h 56mMultiple Airlines
Deal found 11/5$371
This Mytrip deal was found by Cheapflights users on 11/4. 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 11/2111:12 amSWF - PUJ
2 stops27h 13mMultiple Airlines
Sun 11/233:11 pmPUJ - SWF
2 stops19h 56mMultiple Airlines
Deal found 11/4$394
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/1012:01 pmSWF - PUJ
2 stops23h 44mMultiple Airlines
Thu 11/134:25 pmPUJ - SWF
1 stop18h 46mMultiple Airlines
Deal found 11/5$404
This Mytrip deal was found by Cheapflights users on 11/5. 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
Sun 12/213:43 amSTI - SWF
1 stop16h 52mMultiple Airlines
Deal found 11/5$410
This Mytrip deal was found by Cheapflights users on 11/5. 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
Sun 12/283:43 amSTI - SWF
1 stop8h 04mMultiple Airlines
Deal found 11/5$417
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 - STI
1 stop13h 15mMultiple Airlines
Sun 1/184:40 pmSTI - SWF
1 stop18h 39mMultiple Airlines
Deal found 11/6$425
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 - STI
1 stop13h 15mMultiple Airlines
Thu 1/154:40 pmSTI - SWF
1 stop18h 39mMultiple Airlines
Deal found 11/6$443
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/6$455
This Mytrip deal was found by Cheapflights users on 11/6. 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 11/2111:12 amSWF - PUJ
2 stops27h 13mMultiple Airlines
Tue 11/257:00 amPUJ - SWF
3 stops29h 27mMultiple Airlines
Deal found 11/6$493
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/1012:01 pmSWF - STI
1 stop23h 21mMultiple Airlines
Thu 11/131:17 pmSTI - SWF
1 stop21h 54mMultiple Airlines
Deal found 11/5$506

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 November 6, 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

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

$333

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

Thu 1/22

4:40 pm-10:19 am

1 stop18h 39m

$344

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 1/22

4:40 pm-10:19 am

1 stop18h 39m

$344

New WindsorSanto Domingo

SWF - SDQ

SWFSDQ

New Windsor Stewart

Fri 1/9

11:09 am-3:35 pm

1 stop27h 26m

Santo Domingo Las Americas

Thu 2/5

4:40 pm-10:19 am

1 stop18h 39m

$356

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

Sun 12/14

3:43 am-11:37 am

1 stop8h 54m

$360

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 11/17

12:01 pm-12:45 pm

2 stops23h 44m

Punta Cana

Sun 11/23

3:11 pm-10:07 am

2 stops19h 56m

$371

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Fri 11/21

11:12 am-3:25 pm

2 stops27h 13m

Punta Cana

Sun 11/23

3:11 pm-10:07 am

2 stops19h 56m

$394

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Mon 11/10

12:01 pm-12:45 pm

2 stops23h 44m

Punta Cana

Thu 11/13

4:25 pm-10:11 am

1 stop18h 46m

$404

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 12/15

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Sun 12/28

3:43 am-10:47 am

1 stop8h 04m

$417

New WindsorPunta Cana

SWF - PUJ

SWFPUJ

New Windsor Stewart

Sat 12/20

9:45 am-2:09 pm

1 stop27h 24m

Punta Cana

Thu 12/25

6:08 pm-11:07 am

1 stop17h 59m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 50 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, March is the cheapest month in which you can book a flight from New Windsor to Dominican Republic (average of $186). 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.

What is the cheapest time of day to fly from SWF to DO?

Find hourly flight availability from Stewart to Dominican Republic. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from New Windsor to Dominican Republic in the afternoon. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight in the morning.

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, March is the cheapest month in which you can book a flight from New Windsor to Dominican Republic (average of $186). 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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