HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$93+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SWF
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Virginia to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 3, 2025.

This Mytrip deal was found by Cheapflights users on 11/1. 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 11/1$187
This Mytrip deal was found by Cheapflights users on 11/2. 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 11/2$212
This Kiwi.com deal was found by Cheapflights users on 11/2. 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
Mon 1/127:33 pmSWF - RDU
1 stop23h 04mMultiple Airlines
Deal found 11/2$221
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/175:07 pmRIC - SWF
1 stop17h 19mMultiple Airlines
Fri 11/2111:12 amSWF - RIC
1 stop23h 17mMultiple Airlines
Deal found 11/2$224
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/59:31 amIAD - SWF
1 stop7h 23mMultiple Airlines
Sun 12/711:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 11/2$231
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/2$232
This Kiwi.com deal was found by Cheapflights users on 11/2. 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
Mon 12/157:30 pmSWF - RDU
1 stop14h 17mMultiple Airlines
Deal found 11/2$245
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/118:11 pmORF - SWF
1 stop15h 26mMultiple Airlines
Sun 12/1411:43 amSWF - ORF
1 stop20h 00mMultiple Airlines
Deal found 11/2$247
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/1411:09 amSWF - IAD
1 stop21h 22mMultiple Airlines
Deal found 11/3$260
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/68:14 pmRDU - SWF
1 stop14h 49mMultiple Airlines
Mon 12/87:30 pmSWF - RDU
1 stop14h 17mMultiple Airlines
Deal found 11/3$282
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/49:49 pmRIC - SWF
2 stops13h 55mMultiple Airlines
Sun 12/711:09 amSWF - RIC
1 stop22h 03mMultiple Airlines
Deal found 11/3$299
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/123:07 pmRDU - SWF
1 stop19h 56mBreeze Airways
Mon 11/1712:24 pmSWF - RDU
2 stops21h 23mBreeze Airways
Deal found 11/1$301

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 3, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$212
(Mytrip)

One-way from

$93
(Mytrip)

Popular in

November

Cheapest in

January

Average price

$258
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. 8% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 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 3, 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

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Thu 12/11

6:25 pm-11:37 am

1 stop17h 12m

New Windsor Stewart

Mon 12/15

12:27 pm-8:54 pm

1 stop8h 27m

$187

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

$212

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 12/11

9:49 pm-11:44 am

2 stops13h 55m

New Windsor Stewart

Mon 1/12

7:33 pm-6:37 pm

1 stop23h 04m

$221

RichmondNew Windsor

RIC - SWF

RICSWF

Richmond Byrd Intl

Mon 11/17

5:07 pm-10:26 am

1 stop17h 19m

New Windsor Stewart

Fri 11/21

11:12 am-10:29 am

1 stop23h 17m

$224

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 12/5

9:31 am-4:54 pm

1 stop7h 23m

New Windsor Stewart

Sun 12/7

11:43 am-8:24 pm

1 stop8h 41m

$231

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

$232

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Thu 12/11

9:49 pm-11:44 am

2 stops13h 55m

New Windsor Stewart

Mon 12/15

7:30 pm-9:47 am

1 stop14h 17m

$245

NorfolkNew Windsor

ORF - SWF

ORFSWF

Norfolk

Thu 12/11

8:11 pm-11:37 am

1 stop15h 26m

New Windsor Stewart

Sun 12/14

11:43 am-7:43 am

1 stop20h 00m

$247

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

11:09 am-8:31 am

1 stop21h 22m

$260

RaleighNew Windsor

RDU - SWF

RDUSWF

Raleigh-Durham

Sat 12/6

8:14 pm-11:03 am

1 stop14h 49m

New Windsor Stewart

Mon 12/8

7:30 pm-9:47 am

1 stop14h 17m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 60 results
1
2
3
...
6

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 27h 21m. Fly via Allegiant Air to get the fastest option. Airlines will cover a distance of 564 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Virginia to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
O'Hare Intl to John F Kennedy Intl flights
Dallas/Fort Worth to Newark flights
Los Angeles to Newark flights
San Francisco to John F Kennedy Intl flights
Atlanta to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
San Francisco to Newark flights
Hobby to LaGuardia flights
Fort Lauderdale to Newark flights
Hobby to Newark flights
Los Angeles to LaGuardia flights
Seattle to John F Kennedy Intl flights
Atlanta to LaGuardia flights
Hobby to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
Miami to John F Kennedy Intl flights
Miami to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
O'Hare Intl to Newark flights
Fort Lauderdale to LaGuardia flights
Denver to John F Kennedy Intl flights
San Francisco to LaGuardia flights
Charlotte to John F Kennedy Intl flights
George Bush Intcntl to John F Kennedy Intl flights
George Bush Intcntl to Newark flights
Seattle to Newark flights
Atlanta to Newark flights
Austin to John F Kennedy Intl flights
Denver to LaGuardia flights
George Bush Intcntl to LaGuardia flights
Detroit to John F Kennedy Intl flights
Raleigh to LaGuardia flights
Tampa to Newark flights
Minneapolis to John F Kennedy Intl flights
Miami to LaGuardia flights
Tampa to John F Kennedy Intl flights
Raleigh to John F Kennedy Intl flights
Sky Harbor Intl to John F Kennedy Intl flights
Tampa to LaGuardia flights
Indianapolis to John F Kennedy Intl flights
San Diego to John F Kennedy Intl flights
Orlando to LaGuardia flights
Denver to Newark flights
Minneapolis to Newark flights
Orlando to Newark flights
Minneapolis to LaGuardia flights
Midway to Newark flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.