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Stewart

$83+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

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.
Thu 12/2512:38 pmORF - SWF
1 stop23h 06mMultiple Airlines
Thu 1/111:43 amSWF - ORF
1 stop7h 02mMultiple Airlines
Deal found 12/17$512
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.
Thu 12/2512:38 pmORF - SWF
1 stop23h 06mBreeze Airways
Mon 12/2912:24 pmSWF - ORF
1 stop19h 39mBreeze Airways
Deal found 12/17$555
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.
Thu 12/2512:38 pmORF - SWF
2 stops22h 29mMultiple Airlines
Mon 12/2912:24 pmSWF - ORF
1 stop19h 39mMultiple Airlines
Deal found 12/17$556
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.
Wed 12/247:05 amORF - SWF
1 stop9h 39mMultiple Airlines
Thu 12/2511:43 amSWF - ORF
1 stop7h 02mMultiple Airlines
Deal found 12/17$665
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.
Fri 12/262:34 pmORF - SWF
2 stops44h 29mMultiple Airlines
Wed 12/315:34 pmSWF - ORF
1 stop25h 11mMultiple Airlines
Deal found 12/17$684
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.
Sun 12/217:40 pmORF - SWF
2 stops16h 04mMultiple Airlines
Tue 12/2311:43 amSWF - ORF
1 stop7h 02mMultiple Airlines
Deal found 12/17$726
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:40 pmORF - SWF
2 stops22h 26mMultiple Airlines
Mon 12/228:25 pmSWF - ORF
2 stops22h 20mMultiple Airlines
Deal found 12/16$778
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 12/2010:05 pmORF - SWF
2 stops19h 33mMultiple Airlines
Tue 12/2311:43 amSWF - ORF
1 stop7h 02mMultiple Airlines
Deal found 12/17$834
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/171:56 pmORF - SWF
1 stop21h 07mMultiple Airlines
Sat 12/209:45 amSWF - ORF
1 stop28h 29mMultiple Airlines
Deal found 12/16$857

Find 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 December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$232
(Kiwi.com)

One-way from

$83
(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 Beach to New Windsor Stewart
Search Deals
One-way flight from Virginia Beach 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 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 December 18, 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

Thu 1/8

7:33 pm-10:19 am

1 stop14h 46m

New Windsor Stewart

Sun 1/11

10:48 am-10:26 pm

1 stop11h 38m

$232

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 1/29

9:30 pm-11:31 am

1 stop14h 01m

New Windsor Stewart

Sun 2/1

12:13 pm-9:50 pm

1 stop9h 37m

$265

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sat 2/21

8:44 pm-5:12 pm

2 stops20h 28m

New Windsor Stewart

Sun 3/1

11:52 am-6:26 pm

1 stop6h 34m

$275

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 1/1

12:38 pm-11:44 am

1 stop23h 06m

New Windsor Stewart

Mon 1/5

11:37 am-6:45 pm

2 stops31h 08m

$372

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 12/25

12:38 pm-11:07 am

2 stops22h 29m

New Windsor Stewart

Thu 1/1

11:43 am-6:45 pm

1 stop7h 02m

$521

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 2/19

7:13 pm-11:31 am

2 stops16h 18m

New Windsor Stewart

Sun 2/22

11:48 am-9:50 pm

1 stop10h 02m

$553

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 12/25

12:38 pm-11:07 am

2 stops22h 29m

New Windsor Stewart

Mon 12/29

12:24 pm-8:03 am

1 stop19h 39m

$556

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sun 12/21

7:40 pm-11:44 am

2 stops16h 04m

New Windsor Stewart

Tue 12/23

11:43 am-6:45 pm

1 stop7h 02m

$726

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 1/22

7:33 pm-10:19 am

1 stop14h 46m

$83

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 2/11

7:00 am-10:52 am

2 stops27h 52m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 17 results
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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, June is the cheapest month in which you can book a flight from Virginia Beach to New Windsor (average of $98). Flying from Virginia Beach 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 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, June is the cheapest month in which you can book a flight from Virginia Beach to New Windsor (average of $98). Flying from Virginia Beach 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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Alternative routes for Virginia Beach to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
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