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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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$242
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$226
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. 5% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/119:49 pmRDU - SWF
1 stop20h 51mMultiple Airlines
Mon 12/157:30 pmSWF - RDU
1 stop14h 17mMultiple Airlines
Deal found 9/15$242
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/235:45 amRIC - SWF
1 stop28h 56mMultiple Airlines
Sun 10/267:11 pmSWF - RIC
1 stop14h 01mMultiple Airlines
Deal found 9/15$268
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 10/17:00 pmRDU - SWF
1 stop16h 03mMultiple Airlines
Mon 10/611:01 amSWF - RDU
2 stops24h 29mMultiple Airlines
Deal found 9/16$292
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/207:42 pmRIC - SWF
1 stop14h 40mMultiple Airlines
Sun 11/2311:06 amSWF - RIC
1 stop21h 45mMultiple Airlines
Deal found 9/14$295
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/166:15 amIAD - SWF
2 stops28h 26mMultiple Airlines
Thu 10/2311:43 amSWF - IAD
1 stop7h 24mMultiple Airlines
Deal found 9/16$297
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/99:09 amRDU - SWF
1 stop25h 42mMultiple Airlines
Thu 10/1611:43 amSWF - RDU
1 stop21h 24mMultiple Airlines
Deal found 9/16$302
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 11/1410:14 amIAD - SWF
1 stop8h 01mAllegiant Air
Sun 11/166:14 pmSWF - IAD
2 stops24h 23mAllegiant Air
Deal found 9/15$303
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/99:09 amRDU - SWF
1 stop25h 42mMultiple Airlines
Mon 10/1311:01 amSWF - RDU
2 stops21h 54mMultiple Airlines
Deal found 9/15$303
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 9/246:45 amRDU - SWF
2 stops28h 18mMultiple Airlines
Sun 9/2811:43 amSWF - RDU
1 stop21h 24mMultiple Airlines
Deal found 9/16$318
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Wed 9/243:07 pmRDU - SWF
1 stop19h 56mBreeze Airways
Sun 9/2811:43 amSWF - RDU
1 stop28h 09mBreeze Airways
Deal found 9/16$320
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/29:36 pmORF - SWF
1 stop14h 08mMultiple Airlines
Sun 10/57:11 pmSWF - ORF
1 stop27h 07mMultiple Airlines
Deal found 9/17$325
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/207:42 pmRIC - SWF
1 stop14h 40mMultiple Airlines
Mon 11/2410:57 amSWF - RIC
1 stop7h 40mMultiple Airlines
Deal found 9/14$335

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 September 17, 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 12/11

9:49 pm-6:40 pm

1 stop20h 51m

New Windsor Stewart

Mon 12/15

7:30 pm-9:47 am

1 stop14h 17m

$242

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Thu 10/23

5:45 am-10:41 am

1 stop28h 56m

New Windsor Stewart

Sun 10/26

7:11 pm-9:12 am

1 stop14h 01m

$268

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Wed 10/1

7:00 pm-11:03 am

1 stop16h 03m

New Windsor Stewart

Mon 10/6

11:01 am-11:30 am

2 stops24h 29m

$292

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Thu 11/20

7:42 pm-10:22 am

1 stop14h 40m

New Windsor Stewart

Sun 11/23

11:06 am-8:51 am

1 stop21h 45m

$295

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 10/16

6:15 am-10:41 am

2 stops28h 26m

New Windsor Stewart

Thu 10/23

11:43 am-7:07 pm

1 stop7h 24m

$297

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 10/9

9:09 am-10:51 am

1 stop25h 42m

New Windsor Stewart

Thu 10/16

11:43 am-9:07 am

1 stop21h 24m

$302

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 10/9

9:09 am-10:51 am

1 stop25h 42m

New Windsor Stewart

Mon 10/13

11:01 am-8:55 am

2 stops21h 54m

$303

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Wed 9/24

6:45 am-11:03 am

2 stops28h 18m

New Windsor Stewart

Sun 9/28

11:43 am-9:07 am

1 stop21h 24m

$318

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Wed 9/24

3:07 pm-11:03 am

1 stop19h 56m

New Windsor Stewart

Sun 9/28

11:43 am-3:52 pm

1 stop28h 09m

$320

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 10/2

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Sun 10/5

7:11 pm-10:18 pm

1 stop27h 07m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 60 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 19h 07m. Fly via Allegiant Air to get the fastest option. Airlines will cover a distance of 487 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, Norfolk - New Windsor Stewart and Richmond Byrd Intl - 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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