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Stewart

$86+ Cheap flights from Virginia to New Windsor (SWF)

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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap flight deals from Virginia to Stewart

Cheapest flights from Virginia to Stewart
Explore the most affordable flight options available from Virginia to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/298:25 pmRIC - SWF
1 stop14h 38mMultiple Airlines
Fri 1/212:24 pmSWF - RIC
1 stop19h 21mMultiple Airlines
Deal found 12/20$467
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/298:14 pmRDU - SWF
1 stop14h 49mMultiple Airlines
Sat 1/38:45 pmSWF - RDU
1 stop13h 32mMultiple Airlines
Deal found 12/20$567
This CheapOair deal was found by Cheapflights users on 12/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:37 pmRDU - SWF
1 stop13h 26mBreeze Airways
Thu 1/111:43 amSWF - RDU
1 stop21h 24mBreeze Airways
Deal found 12/18$669
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/263:32 pmROA - SWF
1 stop28h 23mAllegiant Air
Mon 12/2912:52 pmSWF - ROA
1 stop7h 43mAllegiant Air
Deal found 12/20$670
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/248:14 pmRDU - SWF
1 stop14h 49mMultiple Airlines
Sat 12/278:45 pmSWF - RDU
1 stop11h 43mMultiple Airlines
Deal found 12/20$674
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/289:58 pmIAD - SWF
2 stops13h 46mMultiple Airlines
Tue 12/3011:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/20$692
This CheapOair deal was found by Cheapflights users on 12/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:07 pmRDU - SWF
1 stop19h 56mBreeze Airways
Sun 1/411:43 amSWF - RDU
1 stop21h 24mBreeze Airways
Deal found 12/20$707
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/229:37 pmRDU - SWF
1 stop13h 26mMultiple Airlines
Tue 12/236:28 pmSWF - RDU
2 stops22h 27mMultiple Airlines
Deal found 12/21$708
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/208:25 pmRIC - SWF
1 stop14h 38mMultiple Airlines
Tue 12/236:28 pmSWF - RIC
2 stops25h 02mMultiple Airlines
Deal found 12/19$710
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Sat 12/278:26 pmIAD - SWF
2 stops14h 37mMultiple Airlines
Tue 12/3011:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/17$715
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/227:40 pmORF - SWF
1 stop15h 23mMultiple Airlines
Thu 12/2511:43 amSWF - ORF
1 stop7h 02mMultiple Airlines
Deal found 12/20$725
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/229:48 pmGSO - SWF
1 stop18h 12mAllegiant Air
Tue 12/304:50 pmSWF - GSO
1 stop21h 37mAllegiant Air
Deal found 12/19$731

Find flight deals from Virginia to Stewart

Keep the following information in mind while searching for Virginia to Stewart flight deals. Data was last updated December 21, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$218
(Kiwi.com)

One-way from

$86
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$260
Provider with most accurate pricing for Norfolk-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-New York (NYC) flights.
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From Virginia to New Windsor Stewart
Search Deals
One-way flight from Virginia to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 Virginia to Stewart 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 21, 2025.
Use the filters below to find and compare flights from Virginia to New Windsor that are best for you.

Fly from

Virginia

Fly to

Stewart

Route

Depart

Return

Price

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 1/22

3:08 pm-10:19 am

1 stop19h 11m

New Windsor Stewart

Sun 1/25

12:13 pm-9:05 am

1 stop20h 52m

$218

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sun 1/11

9:30 pm-11:31 am

1 stop14h 01m

New Windsor Stewart

Sun 1/18

12:13 pm-9:50 pm

1 stop9h 37m

$305

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 2/12

9:59 pm-10:14 am

1 stop12h 15m

New Windsor Stewart

Sun 2/15

7:28 pm-9:52 am

1 stop14h 24m

$316

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sun 6/14

9:50 pm-11:35 am

1 stop13h 45m

New Windsor Stewart

Wed 6/17

12:05 pm-9:45 pm

2 stops9h 40m

$376

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Sun 1/4

8:25 pm-11:44 am

2 stops15h 19m

New Windsor Stewart

Thu 1/8

10:48 am-2:30 pm

1 stop27h 42m

$381

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Sun 1/4

9:58 pm-11:44 am

2 stops13h 46m

New Windsor Stewart

Thu 1/8

12:13 pm-7:55 am

1 stop19h 42m

$394

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sun 1/4

12:38 pm-11:44 am

1 stop23h 06m

New Windsor Stewart

Thu 1/8

12:13 pm-9:50 pm

1 stop9h 37m

$399

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Sat 1/17

5:10 pm-11:33 am

1 stop18h 23m

New Windsor Stewart

Mon 1/19

7:33 pm-10:00 am

1 stop14h 27m

$453

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 1/29

9:36 pm-11:31 am

2 stops13h 55m

New Windsor Stewart

Sun 2/1

12:13 pm-9:01 pm

1 stop8h 48m

$472

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Wed 2/25

9:25 pm-11:08 am

1 stop13h 43m

New Windsor Stewart

Mon 3/2

12:11 pm-9:41 pm

2 stops9h 30m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 46 results
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Best time to book a flight from Virginia to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Virginia 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 Virginia to New Windsor

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

Currently, June is the cheapest month in which you can book a flight from Virginia to New Windsor (average of $98). Flying from Virginia to New Windsor in October is currently the most expensive (average of $179). 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 Virginia to Stewart. 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 into for flights to New Windsor from Virginia?

    If you book a flight to New Windsor from Virginia, you will be flying to Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor.

  • How long is the flight from Virginia to New Windsor?

    There are many flights that can get you from Virginia to New Windsor in 10h 22m. Fly via Breeze Airways or Allegiant Air to get the fastest option. Airlines will cover a distance of 426 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Virginia to New Windsor?

    The most popular flight routes from Virginia to New Windsor are Raleigh-Durham - New Windsor Stewart, Washington, D.C. Dulles Intl - New Windsor Stewart and Norfolk - New Windsor Stewart.

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

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

  • How can I find direct flights from Virginia to Stewart?

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

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

    Yes. Cheapflights offers flight deals from Virginia to Stewart 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 Virginia to New Windsor?

    Currently, June is the cheapest month in which you can book a flight from Virginia to New Windsor (average of $98). Flying from Virginia to New Windsor in October is currently the most expensive (average of $179). 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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