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Stewart

$100+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — SWF
ago. 23 — ago. 301
sáb. 8/23
sáb. 8/30
1 adult, Economy
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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 agosto 18, 2025.

Round-trip from

$210
(Mytrip)

One-way from

$110
(Mytrip)

Popular in

November

Cheapest in

August

Average price

$229
From Pennsylvania to New Windsor Stewart
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One-way flight from Pennsylvania to New Windsor Stewart
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Highest demand for flights based on searches. 18% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 agosto 18, 2025.

This Mytrip deal was found by Cheapflights users on 8/17. 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.
lun. 11/109:00 pmPIT - SWF
1 stop13h 26mMultiple Airlines
lun. 11/1712:01 pmSWF - PIT
1 stop10h 36mMultiple Airlines
Deal found 8/17$210
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/145:01 amPHL - SWF
1 stop13h 21mMultiple Airlines
dom. 9/217:12 pmSWF - PHL
1 stop27h 21mMultiple Airlines
Deal found 8/17$253
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3112:36 pmPIT - SWF
1 stop5h 13mAllegiant Air
dom. 11/26:16 pmSWF - PIT
1 stop25h 58mAllegiant Air
Deal found 8/17$269
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/2410:09 amIAD - SWF
1 stop9h 07mAllegiant Air
dom. 10/267:11 pmSWF - IAD
2 stops25h 24mAllegiant Air
Deal found 8/18$295
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/312:36 pmPIT - SWF
1 stop5h 13mAllegiant Air
dom. 10/57:11 pmSWF - PIT
1 stop25h 05mAllegiant Air
Deal found 8/17$295
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
vie. 10/2410:09 amIAD - SWF
1 stop9h 07mMultiple Airlines
dom. 10/267:11 pmSWF - IAD
1 stop23h 34mMultiple Airlines
Deal found 8/16$314
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
jue. 10/211:29 amPIT - SWF
1 stop5h 26mAllegiant Air
dom. 10/57:11 pmSWF - PIT
1 stop25h 05mAllegiant Air
Deal found 8/16$317
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/2410:20 amPIT - SWF
1 stop7h 40mMultiple Airlines
vie. 8/2912:17 pmSWF - PIT
1 stop8h 49mMultiple Airlines
Deal found 8/18$328
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1012:36 pmPIT - SWF
1 stop5h 13mMultiple Airlines
lun. 10/1311:01 amSWF - PIT
1 stop7h 59mMultiple Airlines
Deal found 8/17$340
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
mié. 10/88:45 pmPIT - SWF
1 stop21h 36mMultiple Airlines
lun. 10/1311:01 amSWF - PIT
1 stop12h 15mMultiple Airlines
Deal found 8/16$344
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
lun. 10/136:15 amABE - SWF
1 stop28h 11mAllegiant Air
jue. 10/167:11 pmSWF - ABE
1 stop16h 46mAllegiant Air
Deal found 8/18$356
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
jue. 10/911:29 amPIT - SWF
1 stop5h 26mMultiple Airlines
lun. 10/1311:01 amSWF - PIT
1 stop7h 59mMultiple Airlines
Deal found 8/18$356

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 agosto 18, 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

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

lun. 11/10

9:00 pm-10:26 am

1 stop13h 26m

New Windsor Stewart

lun. 11/17

12:01 pm-10:37 pm

1 stop10h 36m

$210

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

dom. 9/14

5:01 am-6:22 pm

1 stop13h 21m

New Windsor Stewart

dom. 9/21

7:12 pm-10:33 pm

1 stop27h 21m

$253

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

vie. 10/31

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

dom. 11/2

6:16 pm-8:14 pm

1 stop25h 58m

$269

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

vie. 10/24

10:09 am-7:16 pm

1 stop9h 07m

New Windsor Stewart

dom. 10/26

7:11 pm-8:35 pm

2 stops25h 24m

$295

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

vie. 10/3

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

dom. 10/5

7:11 pm-8:16 pm

1 stop25h 05m

$295

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

vie. 10/24

10:09 am-7:16 pm

1 stop9h 07m

New Windsor Stewart

dom. 10/26

7:11 pm-6:45 pm

1 stop23h 34m

$314

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

jue. 10/2

11:29 am-4:55 pm

1 stop5h 26m

New Windsor Stewart

dom. 10/5

7:11 pm-8:16 pm

1 stop25h 05m

$317

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

dom. 8/24

10:20 am-6:00 pm

1 stop7h 40m

New Windsor Stewart

vie. 8/29

12:17 pm-9:06 pm

1 stop8h 49m

$328

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

vie. 10/10

12:36 pm-5:49 pm

1 stop5h 13m

New Windsor Stewart

lun. 10/13

11:01 am-7:00 pm

1 stop7h 59m

$340

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

mié. 10/8

8:45 pm-6:21 pm

1 stop21h 36m

New Windsor Stewart

lun. 10/13

11:01 am-11:16 pm

1 stop12h 15m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 48 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, October is the cheapest month in which you can book a flight from Pennsylvania to New Windsor (average of $109). Flying from Pennsylvania to New Windsor in December is currently the most expensive (average of $202). 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 agosto 18, 2025.

When flying from Pennsylvania to New Windsor, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 can get you from Pennsylvania to New Windsor in just under 5h 13m. Your travel time can differ by up to . The distance from Pennsylvania to New Windsor is about 327 mi.

  • 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, October is the cheapest month in which you can book a flight from Pennsylvania to New Windsor (average of $109). Flying from Pennsylvania to New Windsor in December is currently the most expensive (average of $202). 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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