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Stewart

$88+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — SWF
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
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 December 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/193:03 pmMDT - SWF
1 stop17h 52mAllegiant Air
Sat 12/207:50 pmSWF - MDT
1 stop19h 10mAllegiant Air
Deal found 12/14$413
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/183:36 pmPIT - SWF
1 stop25h 02mAllegiant Air
Sat 12/207:50 pmSWF - PIT
1 stop25h 41mAllegiant Air
Deal found 12/14$504
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/299:58 pmIAD - SWF
1 stop13h 05mMultiple Airlines
Fri 1/211:57 amSWF - IAD
2 stops20h 53mMultiple Airlines
Deal found 12/14$510
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/198:00 amPIT - SWF
1 stop10h 06mMultiple Airlines
Sat 12/209:45 amSWF - PIT
1 stop13h 34mMultiple Airlines
Deal found 12/14$533
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/171:10 pmMDT - SWF
1 stop21h 09mAllegiant Air
Sat 12/207:50 pmSWF - MDT
1 stop19h 10mAllegiant Air
Deal found 12/14$541
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/228:00 amPIT - SWF
1 stop8h 38mAllegiant Air
Wed 12/2410:40 amSWF - PIT
1 stop30h 15mAllegiant Air
Deal found 12/13$547
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/192:32 pmIAD - SWF
2 stops18h 23mMultiple Airlines
Sun 12/2111:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/13$557
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/178:01 pmPIT - SWF
1 stop14h 18mAllegiant Air
Fri 12/198:11 pmSWF - PIT
1 stop27h 08mAllegiant Air
Deal found 12/14$578
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Tue 12/309:58 pmIAD - SWF
1 stop18h 46mMultiple Airlines
Sun 1/411:43 amSWF - IAD
1 stop9h 20mMultiple Airlines
Deal found 12/15$595
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/198:00 amPIT - SWF
1 stop10h 06mMultiple Airlines
Sun 12/2111:43 amSWF - PIT
1 stop11h 24mMultiple Airlines
Deal found 12/15$598
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/198:00 amPIT - SWF
1 stop10h 06mMultiple Airlines
Fri 12/198:11 pmSWF - PIT
2 stops18h 00mMultiple Airlines
Deal found 12/15$614
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/319:55 amMDT - SWF
1 stop6h 49mAllegiant Air
Sun 1/410:49 amSWF - MDT
1 stop22h 09mAllegiant Air
Deal found 12/16$618

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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$170
(Mytrip)

One-way from

$88
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$554
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. 23% potential increase in price ($102 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 16, 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

Sun 3/15

3:47 pm-9:02 am

1 stop17h 15m

New Windsor Stewart

Sun 3/22

10:29 am-9:38 am

1 stop23h 09m

$334

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sun 3/8

3:47 pm-10:12 am

1 stop18h 25m

New Windsor Stewart

Sun 3/15

8:40 pm-11:27 pm

1 stop26h 47m

$438

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 3/12

3:47 pm-9:02 am

1 stop17h 15m

New Windsor Stewart

Sun 3/15

8:40 pm-11:27 pm

1 stop26h 47m

$439

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Mon 12/29

9:58 pm-11:03 am

1 stop13h 05m

New Windsor Stewart

Fri 1/2

11:57 am-8:50 am

2 stops20h 53m

$510

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 12/19

8:00 am-6:06 pm

1 stop10h 06m

New Windsor Stewart

Sat 12/20

9:45 am-11:19 pm

1 stop13h 34m

$533

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 12/22

8:00 am-4:38 pm

1 stop8h 38m

New Windsor Stewart

Wed 12/24

10:40 am-4:55 pm

1 stop30h 15m

$547

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 1/15

8:43 pm-11:31 am

2 stops14h 48m

New Windsor Stewart

Sun 1/18

12:13 pm-10:03 pm

1 stop9h 50m

$558

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 12/19

8:00 am-6:06 pm

1 stop10h 06m

New Windsor Stewart

Fri 12/19

8:11 pm-11:19 pm

1 stop27h 08m

$578

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 3/12

3:47 pm-9:02 am

1 stop17h 15m

New Windsor Stewart

Sun 3/15

8:40 pm-8:45 pm

2 stops24h 05m

$585

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Tue 12/30

9:58 pm-4:44 pm

1 stop18h 46m

New Windsor Stewart

Sun 1/4

11:43 am-9:03 pm

1 stop9h 20m

$595

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 46 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 January is currently the most expensive (average of $71). 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 December 16, 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.

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

    Allegiant Air can get you from Pennsylvania to New Windsor in just under 18h 25m. 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 Harrisburg - 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 January is currently the most expensive (average of $71). 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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