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Stewart

$105+ Cheap flights from Pennsylvania 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — SWF
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap flight deals from Pennsylvania to Stewart

Cheapest flights from Pennsylvania to Stewart
Explore the most affordable flight options available from Pennsylvania to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sun 4/198:09 am
IAD
-
SWF
1 stop26h 46m
Multiple Airlines
Fri 4/2411:40 am
SWF
-
IAD
1 stop19h 47m
Multiple Airlines
Deal found 2/1$226
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Sun 4/198:09 am
IAD
-
SWF
1 stop26h 46m
Multiple Airlines
Sun 4/2611:45 am
SWF
-
IAD
2 stops21h 11m
Multiple Airlines
Deal found 2/1$264
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 5/178:09 am
IAD
-
SWF
1 stop26h 46m
Multiple Airlines
Sun 5/318:10 pm
SWF
-
IAD
2 stops19h 36m
Multiple Airlines
Deal found 1/31$337
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Tue 6/235:49 pm
PIT
-
SWF
1 stop17h 36m
Multiple Airlines
Mon 6/295:55 pm
SWF
-
PIT
1 stop5h 16m
Multiple Airlines
Deal found 1/31$383
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 2/186:00 am
PIT
-
SWF
1 stop29h 32m
Multiple Airlines
Sun 2/2211:48 am
SWF
-
PIT
1 stop11h 37m
Multiple Airlines
Deal found 2/2$392
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 6/1211:33 am
PIT
-
SWF
1 stop7h 05m
Allegiant Air
Mon 6/155:55 pm
SWF
-
PIT
1 stop5h 16m
Allegiant Air
Deal found 2/1$403
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 7/15:29 pm
PIT
-
SWF
1 stop15h 29m
Multiple Airlines
Sun 7/126:30 pm
SWF
-
PIT
1 stop28h 17m
Multiple Airlines
Deal found 2/1$413
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/56:00 am
PIT
-
SWF
1 stop28h 19m
Multiple Airlines
Mon 2/911:09 am
SWF
-
PIT
1 stop22h 31m
Multiple Airlines
Deal found 2/2$426
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Fri 6/121:28 pm
PIT
-
SWF
2 stops21h 57m
Multiple Airlines
Mon 6/155:55 pm
SWF
-
PIT
1 stop5h 16m
Multiple Airlines
Deal found 2/1$445
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Thu 4/238:09 am
IAD
-
SWF
2 stops9h 40m
Multiple Airlines
Sun 4/2611:48 am
SWF
-
IAD
1 stop19h 39m
Multiple Airlines
Deal found 2/1$450
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 6/2211:33 am
PIT
-
SWF
1 stop7h 05m
Allegiant Air
Mon 6/295:55 pm
SWF
-
PIT
1 stop5h 16m
Allegiant Air
Deal found 1/31$450
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 6/2712:48 pm
PIT
-
SWF
1 stop5h 07m
Allegiant Air
Mon 6/295:55 pm
SWF
-
PIT
1 stop5h 16m
Allegiant Air
Deal found 1/31$469

Find flight deals from Pennsylvania to Stewart

Keep the following information in mind while searching for Pennsylvania to Stewart flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$408
Provider with most accurate pricing for Philadelphia-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Philadelphia-New York (NYC) flights.
Search Deals
From Pennsylvania to New Windsor Stewart
Search Deals
One-way flight from Pennsylvania to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pennsylvania 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 February 3, 2026.
Use the filters below to find and compare flights from Pennsylvania to New Windsor that are best for you.

Fly from

Pennsylvania

Fly to

Stewart

Route

Depart

Return

Price

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Sun 4/19

8:09 am-10:55 am

1 stop26h 46m

New Windsor Stewart

Fri 4/24

11:40 am-7:27 am

1 stop19h 47m

$226

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Sun 4/19

8:09 am-10:55 am

1 stop26h 46m

New Windsor Stewart

Sun 4/26

11:45 am-8:56 am

2 stops21h 11m

$264

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Sun 5/17

8:09 am-10:55 am

1 stop26h 46m

New Windsor Stewart

Sun 5/31

8:10 pm-3:46 pm

2 stops19h 36m

$337

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 2/18

6:00 am-11:32 am

1 stop29h 32m

New Windsor Stewart

Sun 2/22

11:48 am-11:25 pm

1 stop11h 37m

$392

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 7/1

5:29 pm-8:58 am

1 stop15h 29m

New Windsor Stewart

Sun 7/12

6:30 pm-10:47 pm

1 stop28h 17m

$413

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 6/12

1:28 pm-11:25 am

2 stops21h 57m

New Windsor Stewart

Mon 6/15

5:55 pm-11:11 pm

1 stop5h 16m

$445

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 6/22

11:33 am-6:38 pm

1 stop7h 05m

New Windsor Stewart

Mon 6/29

5:55 pm-11:11 pm

1 stop5h 16m

$450

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 4/23

8:09 am-5:49 pm

2 stops9h 40m

New Windsor Stewart

Sun 4/26

11:48 am-7:27 am

1 stop19h 39m

$450

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sat 6/27

12:48 pm-5:55 pm

1 stop5h 07m

New Windsor Stewart

Mon 6/29

5:55 pm-11:11 pm

1 stop5h 16m

$469

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 6/26

11:33 am-6:38 pm

1 stop7h 05m

New Windsor Stewart

Mon 6/29

5:55 pm-11:11 pm

1 stop5h 16m

$481

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 51 results
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Best time to book a flight from Pennsylvania to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Pennsylvania 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 Pennsylvania to New Windsor

What is the cheapest month to book a flight from Pennsylvania to New Windsor?

Currently, April is the cheapest month in which you can book a flight from Pennsylvania to New Windsor (average of $42). Flying from Pennsylvania to New Windsor in December is currently the most expensive (average of $66). 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 Pennsylvania 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 Pennsylvania?

    Most people fly into New Windsor Stewart (SWF) if they book a flight to New Windsor from Pennsylvania. Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

  • How long is the flight from Pennsylvania to New Windsor?

    Allegiant Air and Breeze Airways can get you from Pennsylvania to New Windsor in just under 7h 05m. Your travel time can differ by up to 8h 58m. The distance from Pennsylvania to New Windsor is about 327 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Pennsylvania to New Windsor?

    When deciding which route to take from Pennsylvania to New Windsor consider Pittsburgh - New Windsor Stewart, Harrisburg - New Windsor Stewart or Washington, D.C. Reagan-National - New Windsor Stewart as they are the most popular.

  • Can I find deals for flights from Pennsylvania to Stewart that include hotel bookings?

    Yes. In addition to deals on Pennsylvania to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pennsylvania to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pennsylvania to Stewart.

  • Can I find deals for business class flights from Pennsylvania to Stewart?

    Yes. Cheapflights offers flight deals from Pennsylvania 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 Pennsylvania to New Windsor?

    Currently, April is the cheapest month in which you can book a flight from Pennsylvania to New Windsor (average of $42). Flying from Pennsylvania to New Windsor in December is currently the most expensive (average of $66). 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 Pennsylvania to Stewart

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