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$97+ Cheap flights from New Windsor (SWF) to Pennsylvania

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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PHL
Oct 18 — Oct 251
Sat 10/18
Sat 10/25
1 adult, Economy
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Cheap flight deals from Stewart to Pennsylvania

Keep the following information in mind while searching for Stewart to Pennsylvania flight deals. Data was last updated September 18, 2025.

Round-trip from

$220
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

July

Cheapest in

December
From New Windsor Stewart to Pennsylvania
Search Deals
One-way flight from New Windsor Stewart to Pennsylvania
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($31 potential savings vs. average RT price).
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Find flight deals from Stewart to Pennsylvania

Cheapest flights from Stewart to Pennsylvania
Explore the most affordable flight options available from Stewart to Pennsylvania. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/2411:31 amSWF - PIT
1 stop11h 45mMultiple Airlines
Mon 10/276:45 amPIT - SWF
1 stop7h 26mMultiple Airlines
Deal found 9/16$220
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Mon 10/2011:01 amSWF - PIT
1 stop12h 15mMultiple Airlines
Thu 10/2311:29 amPIT - SWF
1 stop5h 26mMultiple Airlines
Deal found 9/16$238
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/2411:31 amSWF - PIT
1 stop11h 45mMultiple Airlines
Sun 10/2611:29 amPIT - SWF
1 stop5h 26mMultiple Airlines
Deal found 9/16$264
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/312:11 pmSWF - PIT
1 stop11h 12mMultiple Airlines
Mon 10/69:06 pmPIT - SWF
1 stop13h 20mMultiple Airlines
Deal found 9/18$278
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/1011:41 amSWF - PIT
1 stop11h 35mMultiple Airlines
Sun 10/196:51 pmPIT - SWF
1 stop15h 20mMultiple Airlines
Deal found 9/16$285
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/1711:31 amSWF - PIT
1 stop11h 45mMultiple Airlines
Sun 10/1910:24 amPIT - SWF
2 stops23h 47mMultiple Airlines
Deal found 9/15$290
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1611:43 amSWF - IAD
1 stop7h 24mMultiple Airlines
Mon 10/2010:09 amIAD - SWF
1 stop9h 22mMultiple Airlines
Deal found 9/16$301
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:31 amSWF - PHL
1 stop12h 28mMultiple Airlines
Fri 11/75:15 amPHL - SWF
2 stops11h 45mMultiple Airlines
Deal found 9/16$318
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/312:11 pmSWF - PIT
1 stop11h 12mMultiple Airlines
Sun 10/511:29 amPIT - SWF
1 stop5h 26mMultiple Airlines
Deal found 9/18$319
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/1011:41 amSWF - PIT
1 stop11h 35mMultiple Airlines
Sun 10/126:51 pmPIT - SWF
1 stop15h 20mMultiple Airlines
Deal found 9/16$327
This Mytrip deal was found by Cheapflights users on 9/17. 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 10/27:11 pmSWF - IAD
2 stops20h 38mAllegiant Air
Mon 10/610:09 amIAD - SWF
1 stop9h 22mAllegiant Air
Deal found 9/17$351
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/1011:41 amSWF - PHL
1 stop12h 18mMultiple Airlines
Sun 10/126:19 amPHL - SWF
2 stops10h 36mMultiple Airlines
Deal found 9/16$370

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Pennsylvania 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 September 18, 2025.
Use the filters below to find and compare flights from New Windsor to Pennsylvania that are best for you.

Fly from

Stewart

Fly to

Pennsylvania

Route

Depart

Return

Price

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 10/24

11:31 am-11:16 pm

1 stop11h 45m

Pittsburgh

Mon 10/27

6:45 am-2:11 pm

1 stop7h 26m

$220

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Mon 10/20

11:01 am-11:16 pm

1 stop12h 15m

Pittsburgh

Thu 10/23

11:29 am-4:55 pm

1 stop5h 26m

$238

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 10/24

11:31 am-11:16 pm

1 stop11h 45m

Pittsburgh

Sun 10/26

11:29 am-4:55 pm

1 stop5h 26m

$264

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 10/3

12:11 pm-11:23 pm

1 stop11h 12m

Pittsburgh

Mon 10/6

9:06 pm-10:26 am

1 stop13h 20m

$278

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 10/10

11:41 am-11:16 pm

1 stop11h 35m

Pittsburgh

Sun 10/19

6:51 pm-10:11 am

1 stop15h 20m

$285

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 10/17

11:31 am-11:16 pm

1 stop11h 45m

Pittsburgh

Sun 10/19

10:24 am-10:11 am

2 stops23h 47m

$290

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 10/16

11:43 am-7:07 pm

1 stop7h 24m

Washington, D.C. Dulles Intl

Mon 10/20

10:09 am-7:31 pm

1 stop9h 22m

$301

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Fri 10/31

11:31 am-11:59 pm

1 stop12h 28m

Philadelphia

Fri 11/7

5:15 am-5:00 pm

2 stops11h 45m

$318

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 10/3

12:11 pm-11:23 pm

1 stop11h 12m

Pittsburgh

Sun 10/5

11:29 am-4:55 pm

1 stop5h 26m

$319

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 10/10

11:41 am-11:16 pm

1 stop11h 35m

Pittsburgh

Sun 10/12

6:51 pm-10:11 am

1 stop15h 20m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 48 results
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Best time to book a flight from Stewart to Pennsylvania

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

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

Currently, August is the cheapest month in which you can book a flight from New Windsor to Pennsylvania (average of $236). Flying from New Windsor to Pennsylvania in March is currently the most expensive (average of $295). 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 Stewart to Pennsylvania. 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 from for flights from New Windsor to Pennsylvania?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to Pennsylvania from New Windsor.

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

    Departing from New Windsor to Pennsylvania will take you 20h 38m. Airlines will cover a distance of 249 mi.

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

    The most popular flight routes from New Windsor to Pennsylvania are New Windsor Stewart - Pittsburgh, New Windsor Stewart - Washington, D.C. Dulles Intl and New Windsor Stewart - Wilkes-Barre Scranton.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from New Windsor to Pennsylvania (average of $236). Flying from New Windsor to Pennsylvania in March is currently the most expensive (average of $295). 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

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