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Stewart

$128+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Mytrip deal was found by Cheapflights users on 10/28. 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.
Fri 12/58:38 amORF - SWF
1 stop10h 02mMultiple Airlines
Mon 12/812:27 pmSWF - ORF
1 stop6h 49mMultiple Airlines
Deal found 10/28$217
This Mytrip deal was found by Cheapflights users on 10/28. 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 11/137:53 pmORF - SWF
1 stop14h 18mMultiple Airlines
Mon 11/1712:01 pmSWF - ORF
1 stop6h 57mMultiple Airlines
Deal found 10/28$227
This Mytrip deal was found by Cheapflights users on 10/28. 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 11/67:53 pmORF - SWF
1 stop14h 48mMultiple Airlines
Mon 11/1712:01 pmSWF - ORF
1 stop6h 57mMultiple Airlines
Deal found 10/28$248
This Mytrip deal was found by Cheapflights users on 10/29. 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 11/207:18 pmORF - SWF
1 stop15h 04mMultiple Airlines
Sun 11/236:23 pmSWF - ORF
2 stops26h 08mMultiple Airlines
Deal found 10/29$286
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/148:11 pmORF - SWF
1 stop15h 26mMultiple Airlines
Sun 12/216:28 pmSWF - ORF
2 stops43h 38mMultiple Airlines
Deal found 10/30$295
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/126:33 pmORF - SWF
1 stop16h 30mMultiple Airlines
Sun 11/1611:43 amSWF - ORF
1 stop24h 41mMultiple Airlines
Deal found 10/28$316
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Tue 11/258:02 pmORF - SWF
1 stop15h 25mMultiple Airlines
Mon 12/15:49 pmSWF - ORF
2 stops26h 42mMultiple Airlines
Deal found 10/28$319

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 October 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$217
(Mytrip)

One-way from

$128
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$239
Provider with most accurate pricing for Norfolk-New York (NYC) flight deals.
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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. 7% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
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 October 2025
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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 October 30, 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

Fri 12/5

8:38 am-6:40 pm

1 stop10h 02m

New Windsor Stewart

Mon 12/8

12:27 pm-7:16 pm

1 stop6h 49m

$217

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/13

7:53 pm-10:11 am

1 stop14h 18m

New Windsor Stewart

Mon 11/17

12:01 pm-6:58 pm

1 stop6h 57m

$227

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/20

7:18 pm-10:22 am

1 stop15h 04m

New Windsor Stewart

Sun 11/23

6:23 pm-8:31 pm

2 stops26h 08m

$294

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sun 12/14

8:11 pm-11:37 am

1 stop15h 26m

New Windsor Stewart

Sun 12/21

6:28 pm-2:06 pm

2 stops43h 38m

$295

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 12/18

3:01 pm-6:06 pm

1 stop27h 05m

New Windsor Stewart

Mon 12/22

7:10 pm-2:16 pm

1 stop19h 06m

$295

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 11/12

6:33 pm-11:03 am

1 stop16h 30m

New Windsor Stewart

Sun 11/16

11:43 am-12:24 pm

1 stop24h 41m

$316

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Tue 11/25

8:02 pm-11:27 am

1 stop15h 25m

New Windsor Stewart

Mon 12/1

5:49 pm-8:31 pm

2 stops26h 42m

$319

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/27

9:36 pm-11:44 am

1 stop14h 08m

New Windsor Stewart

Thu 12/4

6:28 pm-7:25 am

2 stops36h 57m

$378

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 11/26

9:26 pm-11:03 am

1 stop13h 37m

$128

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 11/6

7:53 pm-10:41 am

1 stop14h 48m

$136

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 13 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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See prices for flight routes from nearby airports that may be better suited for you.
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