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Stewart

$122+ 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Apr 24 — May 11
Fri 4/24
Fri 5/1
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 March 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/169:30 pm
ORF
-
SWF
1 stop14h 01m
Multiple Airlines
Sun 4/1911:45 am
SWF
-
ORF
1 stop8h 17m
Multiple Airlines
Deal found 3/24$277
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 7/269:52 pm
ORF
-
SWF
1 stop13h 45m
Breeze Airways
Wed 7/2912:05 pm
SWF
-
ORF
2 stops8h 50m
Breeze Airways
Deal found 3/22$356
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 8/19:56 pm
ORF
-
SWF
1 stop11h 02m
Multiple Airlines
Wed 8/512:05 pm
SWF
-
ORF
2 stops8h 50m
Multiple Airlines
Deal found 3/21$369
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Wed 8/59:56 pm
ORF
-
SWF
1 stop11h 02m
Multiple Airlines
Fri 8/712:17 pm
SWF
-
ORF
2 stops8h 44m
Multiple Airlines
Deal found 3/20$381
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 6/310:31 pm
ORF
-
SWF
2 stops34h 18m
Multiple Airlines
Mon 6/159:39 am
SWF
-
ORF
1 stop11h 22m
Multiple Airlines
Deal found 3/23$390
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 6/49:12 pm
ORF
-
SWF
2 stops14h 25m
Multiple Airlines
Sun 6/79:38 am
SWF
-
ORF
1 stop10h 39m
Multiple Airlines
Deal found 3/20$400
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Wed 7/12:32 pm
ORF
-
SWF
1 stop18h 26m
Multiple Airlines
Sat 7/412:05 pm
SWF
-
ORF
2 stops8h 50m
Multiple Airlines
Deal found 3/20$404
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 5/810:08 pm
ORF
-
SWF
2 stops13h 17m
Breeze Airways
Mon 5/1112:17 pm
SWF
-
ORF
1 stop21h 03m
Breeze Airways
Deal found 3/22$406

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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(Kiwi.com)

One-way from

$122
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$253
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.
Search Deals
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 ($22 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 March 2026
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 March 25, 2026.
Use the filters below to find and compare flights from Virginia Beach to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sun 7/26

9:52 pm-11:37 am

1 stop13h 45m

New Windsor Stewart

Wed 7/29

12:05 pm-8:55 pm

2 stops8h 50m

$356

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 4/16

9:30 pm-11:31 am

1 stop14h 01m

New Windsor Stewart

Sun 4/19

11:45 am-10:32 am

2 stops22h 47m

$367
Quickest round-trip

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sat 8/1

9:56 pm-8:58 am

1 stop11h 02m

New Windsor Stewart

Wed 8/5

12:05 pm-8:55 pm

2 stops8h 50m

$369

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 8/5

9:56 pm-8:58 am

1 stop11h 02m

New Windsor Stewart

Sat 8/8

12:05 pm-8:55 pm

2 stops8h 50m

$390

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 6/4

9:12 pm-11:37 am

2 stops14h 25m

New Windsor Stewart

Sun 6/7

9:38 am-8:17 pm

1 stop10h 39m

$400

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Wed 7/1

2:32 pm-8:58 am

1 stop18h 26m

New Windsor Stewart

Sat 7/4

12:05 pm-8:55 pm

2 stops8h 50m

$404

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Fri 5/8

10:08 pm-11:25 am

2 stops13h 17m

New Windsor Stewart

Mon 5/11

12:17 pm-9:20 am

1 stop21h 03m

$406

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 8/20

9:52 pm-11:37 am

1 stop13h 45m

New Windsor Stewart

Sun 8/23

1:00 pm-8:39 pm

1 stop7h 39m

$419

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 5/7

9:56 pm-11:37 am

1 stop13h 41m

New Windsor Stewart

Thu 5/14

11:45 am-10:46 pm

2 stops11h 01m

$419

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Fri 6/12

9:56 pm-11:25 am

2 stops13h 29m

New Windsor Stewart

Sun 6/14

9:38 am-9:01 pm

1 stop11h 23m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 17 resultsSorted by cheapest first
1
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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 January 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.

  • How long is the flight from Virginia Beach to New Windsor?

    A quick flight from Virginia Beach to New Windsor can take about 13h 45m. Breeze Airways provides one of the quickest options available for as low as $356. The distance between Virginia Beach and New Windsor is about 337 mi.

  • 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 January 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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