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Pennsylvania

$98+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PHL
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Mytrip deal was found by Cheapflights users on 10/29. 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.
Fri 12/512:27 pmSWF - PHL
1 stop10h 49mMultiple Airlines
Mon 12/85:30 amPHL - SWF
1 stop13h 10mMultiple Airlines
Deal found 10/29$219
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Fri 11/1411:01 amSWF - PHL
1 stop12h 25mMultiple Airlines
Sun 11/168:51 pmPHL - SWF
1 stop14h 20mMultiple Airlines
Deal found 10/28$263
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/1412:24 pmSWF - PIT
1 stop19h 22mMultiple Airlines
Sun 11/1610:15 amPIT - SWF
1 stop24h 56mMultiple Airlines
Deal found 10/28$295
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Fri 12/1212:27 pmSWF - PHL
1 stop10h 49mMultiple Airlines
Fri 12/196:00 amPHL - SWF
1 stop12h 06mMultiple Airlines
Deal found 10/28$300
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/131:32 pmSWF - AVP
1 stop21h 37mMultiple Airlines
Mon 11/1711:49 amAVP - SWF
1 stop5h 48mMultiple Airlines
Deal found 10/29$306
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/2711:43 amSWF - IAD
1 stop20h 07mMultiple Airlines
Thu 12/45:45 amIAD - SWF
2 stops29h 52mMultiple Airlines
Deal found 10/29$311
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/136:14 pmSWF - PIT
1 stop23h 20mAllegiant Air
Mon 11/179:00 pmPIT - SWF
1 stop13h 26mAllegiant Air
Deal found 10/29$340
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/147:05 pmSWF - PIT
1 stop19h 13mAllegiant Air
Mon 11/179:00 pmPIT - SWF
1 stop13h 26mAllegiant Air
Deal found 10/29$343
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/196:56 pmSWF - PIT
1 stop15h 02mMultiple Airlines
Mon 12/2210:53 amPIT - SWF
1 stop8h 42mMultiple Airlines
Deal found 10/28$348
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/711:31 amSWF - PHL
1 stop21h 59mMultiple Airlines
Sun 11/95:05 amPHL - SWF
1 stop30h 06mMultiple Airlines
Deal found 10/29$350
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/911:43 amSWF - PIT
1 stop11h 53mMultiple Airlines
Mon 11/109:00 pmPIT - SWF
1 stop13h 26mMultiple Airlines
Deal found 10/29$357
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/127:30 pmSWF - PIT
1 stop23h 21mMultiple Airlines
Fri 12/198:00 amPIT - SWF
1 stop10h 06mMultiple Airlines
Deal found 10/28$368

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$185
(Mytrip)

One-way from

$98
(Kiwi.com)

Popular in

July

Cheapest in

December

Average price

$484
Provider with most accurate pricing for New York (NYC)-Philadelphia flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Philadelphia flights.
Search Deals
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. 12% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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 1/9

11:09 am-10:37 pm

1 stop11h 28m

Pittsburgh

Sun 1/11

5:44 pm-10:19 am

1 stop16h 35m

$192

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Fri 12/5

12:27 pm-11:16 pm

1 stop10h 49m

Philadelphia

Mon 12/8

5:30 am-6:40 pm

1 stop13h 10m

$219

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Fri 11/14

11:01 am-11:26 pm

1 stop12h 25m

Philadelphia

Sun 11/16

8:51 pm-11:11 am

1 stop14h 20m

$263

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 11/14

12:24 pm-7:46 am

1 stop19h 22m

Pittsburgh

Sun 11/16

10:15 am-11:11 am

1 stop24h 56m

$295

New WindsorPhiladelphia

SWF - PHL

SWFPHL

New Windsor Stewart

Fri 12/12

12:27 pm-11:16 pm

1 stop10h 49m

Philadelphia

Fri 12/19

6:00 am-6:06 pm

1 stop12h 06m

$300

New WindsorScranton

SWF - AVP

SWFAVP

New Windsor Stewart

Thu 11/13

1:32 pm-11:09 am

1 stop21h 37m

Wilkes-Barre Scranton

Mon 11/17

11:49 am-5:37 pm

1 stop5h 48m

$306

New WindsorWashington, D.C.

SWF - IAD

SWFIAD

New Windsor Stewart

Thu 11/27

11:43 am-7:50 am

1 stop20h 07m

Washington, D.C. Dulles Intl

Thu 12/4

5:45 am-11:37 am

2 stops29h 52m

$311

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 11/13

6:14 pm-5:34 pm

1 stop23h 20m

Pittsburgh

Mon 11/17

9:00 pm-10:26 am

1 stop13h 26m

$340

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 11/14

7:05 pm-2:18 pm

1 stop19h 13m

Pittsburgh

Mon 11/17

9:00 pm-10:26 am

1 stop13h 26m

$343

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Sun 11/9

11:43 am-11:36 pm

1 stop11h 53m

Pittsburgh

Mon 11/10

9:00 pm-10:26 am

1 stop13h 26m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 45 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, May is the cheapest month in which you can book a flight from New Windsor to Pennsylvania (average of $31). Flying from New Windsor to Pennsylvania 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 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 23h 20m. Airlines will cover a distance of 327 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 - Philadelphia.

  • 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, May is the cheapest month in which you can book a flight from New Windsor to Pennsylvania (average of $31). Flying from New Windsor to Pennsylvania 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

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