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Stewart

$90+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Aug 27 — Sep 31
Wed 8/27
Wed 9/3
1 adult, Economy
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Cheap flight deals from Virginia to Stewart

Keep the following information in mind while searching for Virginia to Stewart flight deals. Data was last updated August 22, 2025.

Round-trip from

$274
(Kiwi.com)

One-way from

$90
(Mytrip)

Popular in

November

Cheapest in

September

Average price

$229
From Virginia to New Windsor Stewart
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One-way flight from Virginia to New Windsor Stewart
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Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 22, 2025.

This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:12 pmRIC - SWF
1 stop15h 39mMultiple Airlines
Mon 10/1311:01 amSWF - RIC
1 stop7h 00mMultiple Airlines
Deal found 8/19$207
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 10/237:12 pmRIC - SWF
1 stop15h 29mMultiple Airlines
Sun 10/267:11 pmSWF - RIC
1 stop21h 51mMultiple Airlines
Deal found 8/19$220
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 10/307:19 pmRIC - SWF
1 stop15h 22mMultiple Airlines
Sun 11/26:16 pmSWF - RIC
1 stop19h 56mMultiple Airlines
Deal found 8/19$237
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Thu 10/97:12 pmRIC - SWF
1 stop15h 39mMultiple Airlines
Sun 10/127:11 pmSWF - RIC
1 stop13h 16mMultiple Airlines
Deal found 8/20$274
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 11/176:37 pmRDU - SWF
1 stop15h 49mMultiple Airlines
Fri 11/2111:12 amSWF - RDU
1 stop29h 12mMultiple Airlines
Deal found 8/20$305
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/2510:54 amROA - SWF
1 stop7h 28mMultiple Airlines
Sun 9/282:04 pmSWF - ROA
2 stops27h 39mMultiple Airlines
Deal found 8/19$361
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Sun 8/319:15 pmRDU - SWF
1 stop12h 57mMultiple Airlines
Sun 9/77:12 pmSWF - RDU
1 stop21h 59mMultiple Airlines
Deal found 8/19$379
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Tue 11/255:19 pmRDU - SWF
1 stop18h 08mMultiple Airlines
Sun 11/308:41 pmSWF - RDU
1 stop11h 43mMultiple Airlines
Deal found 8/19$416
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Tue 11/257:42 pmRIC - SWF
1 stop15h 45mMultiple Airlines
Mon 12/15:49 pmSWF - RIC
2 stops49h 31mMultiple Airlines
Deal found 8/20$417
This Kiwi.com deal was found by Cheapflights users on 8/20. 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.
Tue 11/257:30 amORF - SWF
1 stop27h 57mMultiple Airlines
Sun 11/308:41 pmSWF - ORF
1 stop22h 56mMultiple Airlines
Deal found 8/20$459
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Fri 8/295:30 amORF - SWF
1 stop7h 35mMultiple Airlines
Mon 9/11:55 pmSWF - ORF
2 stops26h 30mMultiple Airlines
Deal found 8/19$463
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 8/289:15 pmRDU - SWF
1 stop12h 52mMultiple Airlines
Mon 9/11:55 pmSWF - RDU
2 stops33h 20mMultiple Airlines
Deal found 8/19$481

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 August 22, 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

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Thu 10/9

7:12 pm-10:51 am

1 stop15h 39m

New Windsor Stewart

Sun 10/12

7:11 pm-8:27 am

1 stop13h 16m

$274

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Mon 11/17

6:37 pm-10:26 am

1 stop15h 49m

New Windsor Stewart

Fri 11/21

11:12 am-4:24 pm

1 stop29h 12m

$305

RoanokeNew Windsor

ROA - SWF

ROASWF

Roanoke

Thu 9/25

10:54 am-6:22 pm

1 stop7h 28m

New Windsor Stewart

Sun 9/28

2:04 pm-5:43 pm

2 stops27h 39m

$361

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Sun 8/31

9:15 pm-10:12 am

1 stop12h 57m

New Windsor Stewart

Sun 9/7

7:12 pm-5:11 pm

1 stop21h 59m

$379

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Tue 11/25

7:42 pm-11:27 am

1 stop15h 45m

New Windsor Stewart

Mon 12/1

5:49 pm-7:20 pm

2 stops49h 31m

$417

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Tue 11/25

7:30 am-11:27 am

1 stop27h 57m

New Windsor Stewart

Sun 11/30

8:41 pm-7:37 pm

1 stop22h 56m

$459

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 8/28

9:15 pm-10:07 am

1 stop12h 52m

New Windsor Stewart

Mon 9/1

1:55 pm-11:15 pm

2 stops33h 20m

$481

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Tue 11/25

7:42 pm-11:27 am

1 stop15h 45m

New Windsor Stewart

Sun 11/30

8:41 pm-7:20 pm

1 stop22h 39m

$487

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Wed 10/22

3:07 pm-11:03 am

1 stop19h 56m

New Windsor Stewart

Sun 10/26

11:43 am-9:07 am

1 stop21h 24m

$501

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Wed 9/3

3:07 pm-11:03 am

1 stop19h 56m

New Windsor Stewart

Sun 9/7

11:43 am-9:07 am

1 stop21h 24m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 57 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, October is the cheapest month in which you can book a flight from Virginia to New Windsor (average of $109). Flying from Virginia to New Windsor in December is currently the most expensive (average of $202). 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 14h 08m. Fly via Breeze Airways to get the fastest option. Airlines will cover a distance of 337 mi.

  • 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, Richmond Byrd 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, October is the cheapest month in which you can book a flight from Virginia to New Windsor (average of $109). Flying from Virginia to New Windsor in December is currently the most expensive (average of $202). 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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