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Stewart

$126+ Cheap flights from Virginia Beach, VA 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Virginia Beach to Stewart

Keep the following information in mind while searching for Virginia Beach to Stewart flight deals. Data was last updated September 15, 2025.

Round-trip from

$342
(Kiwi.com)

One-way from

$126
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$226
From Virginia Beach to New Windsor Stewart
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One-way flight from Virginia Beach 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 Beach to Stewart

Cheapest flights from Virginia Beach to Stewart
Explore the most affordable flight options available from Virginia Beach to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

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.
Wed 10/2910:05 pmORF - SWF
2 stops14h 40mMultiple Airlines
Fri 10/3111:31 amSWF - ORF
1 stop11h 15mMultiple Airlines
Deal found 9/14$342
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.
Wed 11/268:32 pmORF - SWF
1 stop14h 31mMultiple Airlines
Mon 12/15:49 pmSWF - ORF
2 stops37h 36mMultiple Airlines
Deal found 9/14$356
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.
Wed 11/1210:05 pmORF - SWF
2 stops14h 37mMultiple Airlines
Fri 11/1411:01 amSWF - ORF
1 stop12h 39mMultiple Airlines
Deal found 9/14$366
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/209:36 pmORF - SWF
1 stop14h 08mMultiple Airlines
Sun 11/2311:06 amSWF - ORF
1 stop11h 52mMultiple Airlines
Deal found 9/13$427
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 11/279:36 pmORF - SWF
1 stop14h 08mMultiple Airlines
Mon 12/19:56 amSWF - ORF
1 stop29h 45mMultiple Airlines
Deal found 9/14$447
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.
Wed 11/268:32 pmORF - SWF
1 stop14h 31mMultiple Airlines
Sun 11/308:41 pmSWF - ORF
1 stop25h 21mMultiple Airlines
Deal found 9/14$496
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 10/169:36 pmORF - SWF
1 stop14h 08mBreeze Airways
Mon 10/2012:24 pmSWF - ORF
2 stops9h 38mBreeze Airways
Deal found 9/14$566
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 11/279:36 pmORF - SWF
1 stop14h 08mMultiple Airlines
Sun 11/308:41 pmSWF - ORF
1 stop13h 34mMultiple Airlines
Deal found 9/14$595
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:36 pmORF - SWF
1 stop14h 08mBreeze Airways
Mon 10/2712:24 pmSWF - ORF
2 stops9h 38mBreeze Airways
Deal found 9/13$596
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 11/279:36 pmORF - SWF
1 stop14h 08mBreeze Airways
Mon 12/112:24 pmSWF - ORF
2 stops9h 38mBreeze Airways
Deal found 9/14$604

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia Beach 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 15, 2025.
Use the filters below to find and compare flights from Virginia Beach to New Windsor that are best for you.

Fly from

Virginia Beach

Fly to

Stewart

Route

Depart

Return

Price

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 10/29

10:05 pm-12:45 pm

2 stops14h 40m

New Windsor Stewart

Fri 10/31

11:31 am-10:46 pm

1 stop11h 15m

$342

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 11/26

8:32 pm-11:03 am

1 stop14h 31m

New Windsor Stewart

Mon 12/1

5:49 pm-7:25 am

2 stops37h 36m

$356

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 11/12

10:05 pm-12:42 pm

2 stops14h 37m

New Windsor Stewart

Fri 11/14

11:01 am-11:40 pm

1 stop12h 39m

$366

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/20

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Sun 11/23

11:06 am-10:58 pm

1 stop11h 52m

$427

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/27

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Mon 12/1

9:56 am-3:41 pm

1 stop29h 45m

$447

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 11/26

8:32 pm-11:03 am

1 stop14h 31m

New Windsor Stewart

Sun 11/30

8:41 pm-10:02 pm

1 stop25h 21m

$496

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 10/16

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Mon 10/20

12:24 pm-10:02 pm

2 stops9h 38m

$566

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/27

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Sun 11/30

8:41 pm-10:15 am

1 stop13h 34m

$595

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 10/23

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Mon 10/27

12:24 pm-10:02 pm

2 stops9h 38m

$596

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/27

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Mon 12/1

12:24 pm-10:02 pm

2 stops9h 38m

$604

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 18 results
1
2

Best time to book a flight from Virginia Beach to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Virginia Beach to New Windsor (average of $109). Flying from Virginia Beach 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 Beach 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 Beach?

    For a flight from Virginia Beach to New Windsor, you will be flying into Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city. Stewart is the only New Windsor airport and it handles 0 inbound flights from Virginia Beach per day. 0 airlines have flights to New Windsor Stewart from Virginia Beach on a regular basis.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Virginia Beach to New Windsor (average of $109). Flying from Virginia Beach 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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