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Stewart

$89+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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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 November 19, 2025.

This Mytrip deal was found by Cheapflights users on 11/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:25 pmRIC - SWF
1 stop17h 12mMultiple Airlines
Mon 12/1512:27 pmSWF - RIC
1 stop8h 27mMultiple Airlines
Deal found 11/17$168
This Mytrip deal was found by Cheapflights users on 11/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:25 pmRIC - SWF
1 stop17h 12mMultiple Airlines
Fri 12/1212:27 pmSWF - RIC
1 stop8h 27mMultiple Airlines
Deal found 11/17$170
This Mytrip deal was found by Cheapflights users on 11/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:11 pmORF - SWF
1 stop15h 26mMultiple Airlines
Mon 12/1512:27 pmSWF - ORF
1 stop6h 49mMultiple Airlines
Deal found 11/17$190
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/116:25 pmRIC - SWF
1 stop17h 12mMultiple Airlines
Sun 12/1411:43 amSWF - RIC
1 stop29h 41mMultiple Airlines
Deal found 11/19$221
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/47:11 pmRDU - SWF
2 stops16h 33mMultiple Airlines
Fri 12/57:30 pmSWF - RDU
1 stop13h 27mMultiple Airlines
Deal found 11/17$257
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/148:11 pmORF - SWF
1 stop15h 26mMultiple Airlines
Thu 12/1811:43 amSWF - ORF
1 stop7h 02mMultiple Airlines
Deal found 11/17$258
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/117:11 pmRDU - SWF
2 stops16h 33mMultiple Airlines
Mon 12/157:30 pmSWF - RDU
1 stop14h 17mMultiple Airlines
Deal found 11/16$263
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/47:11 pmRDU - SWF
2 stops16h 33mMultiple Airlines
Mon 12/87:30 pmSWF - RDU
1 stop14h 17mMultiple Airlines
Deal found 11/17$266
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Mon 12/297:40 pmORF - SWF
1 stop15h 23mMultiple Airlines
Sun 1/1112:13 pmSWF - ORF
1 stop9h 37mMultiple Airlines
Deal found 11/18$288
This Kiwi.com deal was found by Cheapflights users on 11/18. 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
2 stops13h 55mMultiple Airlines
Fri 12/127:30 pmSWF - RDU
1 stop13h 27mMultiple Airlines
Deal found 11/18$292
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/129:31 amIAD - SWF
1 stop7h 23mMultiple Airlines
Sun 12/1411:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 11/18$295
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/138:14 pmRDU - SWF
1 stop14h 49mMultiple Airlines
Mon 12/1512:27 pmSWF - RDU
2 stops11h 45mMultiple Airlines
Deal found 11/18$296

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 November 19, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$190
(Mytrip)

One-way from

$89
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$272
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 to New Windsor Stewart
Search Deals
One-way flight from Virginia 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 ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 19, 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

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 12/11

8:11 pm-11:37 am

1 stop15h 26m

New Windsor Stewart

Mon 12/15

12:27 pm-7:16 pm

1 stop6h 49m

$190

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Thu 12/11

6:25 pm-11:37 am

1 stop17h 12m

New Windsor Stewart

Sun 12/14

11:43 am-5:24 pm

1 stop29h 41m

$221

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Sun 12/14

8:11 pm-11:37 am

1 stop15h 26m

New Windsor Stewart

Thu 12/18

11:43 am-6:45 pm

1 stop7h 02m

$258

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 12/4

7:11 pm-11:44 am

2 stops16h 33m

New Windsor Stewart

Mon 12/8

7:30 pm-9:47 am

1 stop14h 17m

$266

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Mon 12/29

7:40 pm-11:03 am

1 stop15h 23m

New Windsor Stewart

Sun 1/11

12:13 pm-9:50 pm

1 stop9h 37m

$288

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 12/11

9:49 pm-11:44 am

2 stops13h 55m

New Windsor Stewart

Fri 12/12

7:30 pm-8:57 am

1 stop13h 27m

$292

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Sat 12/13

8:14 pm-11:03 am

1 stop14h 49m

New Windsor Stewart

Mon 12/15

12:27 pm-12:12 am

2 stops11h 45m

$296

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 12/12

9:31 am-4:54 pm

1 stop7h 23m

New Windsor Stewart

Sun 12/14

11:43 am-8:24 pm

1 stop8h 41m

$304

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Thu 12/18

8:25 pm-6:06 pm

2 stops21h 41m

New Windsor Stewart

Mon 12/22

8:25 pm-5:09 pm

2 stops20h 44m

$305

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Sat 12/6

5:18 pm-10:19 am

1 stop17h 01m

New Windsor Stewart

Mon 12/8

12:27 pm-12:12 am

2 stops11h 45m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

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, June is the cheapest month in which you can book a flight from Virginia to New Windsor (average of $98). Flying from Virginia 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 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 7h 50m. Fly via Allegiant Air to get the fastest option. Airlines will cover a distance of 426 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, Washington, D.C. Dulles Intl - New Windsor Stewart and Norfolk - 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, June is the cheapest month in which you can book a flight from Virginia to New Windsor (average of $98). Flying from Virginia 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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