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Stewart

$103+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — SWF
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

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.
Thu 12/46:58 pmPHL - SWF
1 stop16h 39mMultiple Airlines
Mon 12/812:27 pmSWF - PHL
1 stop12h 09mMultiple Airlines
Deal found 10/28$193
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.
Mon 11/109:00 pmPIT - SWF
1 stop13h 26mMultiple Airlines
Fri 12/512:27 pmSWF - PIT
1 stop27h 43mMultiple Airlines
Deal found 10/28$245
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 11/287:30 amPIT - SWF
1 stop11h 08mMultiple Airlines
Fri 12/512:27 pmSWF - PIT
1 stop27h 43mMultiple Airlines
Deal found 10/29$267
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 12/59:31 amIAD - SWF
1 stop7h 23mMultiple Airlines
Sun 12/711:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 10/29$281
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 12/129:31 amIAD - SWF
1 stop7h 23mMultiple Airlines
Sun 12/1411:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 10/28$282
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.
Wed 12/178:01 pmPIT - SWF
1 stop14h 18mMultiple Airlines
Fri 12/196:56 pmSWF - PIT
1 stop15h 02mMultiple Airlines
Deal found 10/28$324
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 12/117:57 pmIAD - SWF
2 stops20h 57mMultiple Airlines
Sun 12/1411:43 amSWF - IAD
1 stop8h 41mMultiple Airlines
Deal found 10/29$335
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 12/57:10 amPIT - SWF
1 stop11h 30mMultiple Airlines
Mon 12/812:24 pmSWF - PIT
2 stops20h 22mMultiple Airlines
Deal found 10/29$335
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.
Thu 12/181:00 pmPIT - SWF
2 stops29h 06mMultiple Airlines
Mon 12/228:25 pmSWF - PIT
1 stop13h 33mMultiple Airlines
Deal found 10/28$367
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 12/129:31 amIAD - SWF
1 stop7h 23mMultiple Airlines
Fri 12/1912:24 pmSWF - IAD
2 stops20h 27mMultiple Airlines
Deal found 10/28$375
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 11/710:14 amIAD - SWF
1 stop8h 01mMultiple Airlines
Sun 11/96:14 pmSWF - IAD
2 stops22h 20mMultiple Airlines
Deal found 10/29$380
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.
Mon 11/109:00 pmPIT - SWF
1 stop13h 26mAllegiant Air
Thu 11/136:14 pmSWF - PIT
1 stop23h 20mAllegiant Air
Deal found 10/28$402

Cheap flight deals from Pennsylvania to Stewart

Keep the following information in mind while searching for Pennsylvania to Stewart flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$419
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. 15% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 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 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 October 30, 2025.
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

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 12/4

6:58 pm-11:37 am

1 stop16h 39m

New Windsor Stewart

Mon 12/8

12:27 pm-12:36 am

1 stop12h 09m

$193

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 11/10

9:00 pm-10:26 am

1 stop13h 26m

New Windsor Stewart

Fri 12/5

12:27 pm-4:10 pm

1 stop27h 43m

$245

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 11/28

7:30 am-6:38 pm

1 stop11h 08m

New Windsor Stewart

Fri 12/5

12:27 pm-4:10 pm

1 stop27h 43m

$267

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

$281

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

$282

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 12/17

8:01 pm-10:19 am

1 stop14h 18m

New Windsor Stewart

Fri 12/19

6:56 pm-9:58 am

1 stop15h 02m

$324

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 12/11

7:57 pm-4:54 pm

2 stops20h 57m

New Windsor Stewart

Sun 12/14

11:43 am-8:24 pm

1 stop8h 41m

$335

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 12/5

7:10 am-6:40 pm

1 stop11h 30m

New Windsor Stewart

Mon 12/8

12:24 pm-8:46 am

2 stops20h 22m

$335

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 12/18

1:00 pm-6:06 pm

2 stops29h 06m

New Windsor Stewart

Mon 12/22

8:25 pm-9:58 am

1 stop13h 33m

$367

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

Fri 12/19

12:24 pm-8:51 am

2 stops20h 27m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 49 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 November is currently the most expensive (average of $82). 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.

What is the cheapest time of day to fly from PA to SWF?

Find hourly flight availability from Pennsylvania to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s typically best to fly out from Pennsylvania to New Windsor in the afternoon. Doing so could potentially save you 89% on the flight price compared to flying in the morning, which is usually more expensive.

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.

  • 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, Washington, D.C. Dulles Intl - New Windsor Stewart or Philadelphia - 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 November is currently the most expensive (average of $82). 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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