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$96+ Cheap flights from New Windsor to Pittsburgh (SWF - PIT)

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PIT
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Stewart to Pittsburgh

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

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 12/315:34 pmSWF - PIT
1 stop21h 45mAllegiant Air
Sun 1/412:30 pmPIT - SWF
1 stop23h 32mAllegiant Air
Deal found 12/16$488
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 12/315:34 pmSWF - PIT
1 stop21h 45mMultiple Airlines
Sun 1/410:53 amPIT - SWF
2 stops24h 51mMultiple Airlines
Deal found 12/16$562
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Sat 12/209:45 amSWF - PIT
1 stop13h 34mAllegiant Air
Mon 12/228:00 amPIT - SWF
1 stop8h 38mAllegiant Air
Deal found 12/17$582
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/3011:43 amSWF - PIT
1 stop11h 16mMultiple Airlines
Sun 1/410:53 amPIT - SWF
1 stop23h 54mMultiple Airlines
Deal found 12/17$594
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Sun 12/2111:43 amSWF - PIT
1 stop29h 26mMultiple Airlines
Tue 12/236:09 pmPIT - SWF
1 stop22h 35mMultiple Airlines
Deal found 12/17$599
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Fri 12/198:11 pmSWF - PIT
1 stop27h 08mAllegiant Air
Mon 12/228:00 amPIT - SWF
1 stop8h 38mAllegiant Air
Deal found 12/17$601
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Fri 12/1912:24 pmSWF - PIT
2 stops34h 18mMultiple Airlines
Mon 12/228:00 amPIT - SWF
1 stop8h 38mMultiple Airlines
Deal found 12/17$639
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.
Mon 12/228:25 pmSWF - PIT
2 stops26h 34mMultiple Airlines
Tue 12/306:09 pmPIT - SWF
1 stop22h 35mMultiple Airlines
Deal found 12/16$643
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/236:28 pmSWF - PIT
2 stops38h 18mMultiple Airlines
Tue 12/306:09 pmPIT - SWF
1 stop22h 35mMultiple Airlines
Deal found 12/17$644
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.
Mon 12/225:28 pmSWF - PIT
1 stop30h 01mAllegiant Air
Tue 12/306:09 pmPIT - SWF
1 stop22h 35mAllegiant Air
Deal found 12/16$660
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Fri 12/1912:24 pmSWF - PIT
2 stops21h 34mMultiple Airlines
Sun 12/213:36 pmPIT - SWF
1 stop25h 02mMultiple Airlines
Deal found 12/17$682

Find flight deals from Stewart to Pittsburgh

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Pittsburgh (PIT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$167
(Mytrip)

One-way from

$96
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$259
Provider with most accurate pricing for New Windsor Stewart-Pittsburgh flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Pittsburgh flights.
Search Deals
From New Windsor Stewart to Pittsburgh
Search Deals
One-way flight from New Windsor Stewart to Pittsburgh
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 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 Stewart to Pittsburgh 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 18, 2025.
Use the filters below to find and compare flights from New Windsor to Pittsburgh that are best for you.

Fly from

Stewart

Fly to

Pittsburgh

Route

Depart

Return

Price

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 1/30

11:09 am-11:44 pm

1 stop12h 35m

Pittsburgh

Sun 2/1

5:50 pm-10:19 am

1 stop16h 29m

$167

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 1/9

11:09 am-11:44 pm

1 stop12h 35m

Pittsburgh

Sun 1/11

5:50 pm-10:19 am

1 stop16h 29m

$175

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 2/19

7:28 pm-7:40 pm

1 stop24h 12m

Pittsburgh

Sun 2/22

5:45 am-5:12 pm

2 stops11h 27m

$325

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 1/8

12:13 pm-11:07 pm

1 stop10h 54m

Pittsburgh

Tue 1/13

5:50 pm-9:58 am

2 stops40h 08m

$326

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Wed 12/31

5:34 pm-3:19 pm

1 stop21h 45m

Pittsburgh

Sun 1/4

12:30 pm-12:02 pm

1 stop23h 32m

$488

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Wed 12/31

5:34 pm-3:19 pm

1 stop21h 45m

Pittsburgh

Sun 1/4

10:53 am-11:44 am

2 stops24h 51m

$562

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Tue 12/30

11:43 am-10:59 pm

1 stop11h 16m

Pittsburgh

Sun 1/4

10:53 am-10:47 am

1 stop23h 54m

$594

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Sun 12/21

11:43 am-5:09 pm

1 stop29h 26m

Pittsburgh

Tue 12/23

6:09 pm-4:44 pm

1 stop22h 35m

$599

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Mon 12/22

8:25 pm-10:59 pm

2 stops26h 34m

Pittsburgh

Tue 12/30

6:09 pm-4:44 pm

1 stop22h 35m

$643

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Tue 12/23

6:28 pm-8:46 am

2 stops38h 18m

Pittsburgh

Tue 12/30

6:09 pm-4:44 pm

1 stop22h 35m

$644

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 20 results
1
2

Compare providers for flights from Stewart to Pittsburgh

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Pittsburgh in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Pittsburgh flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Pittsburgh flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Pittsburgh flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Pittsburgh flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Pittsburgh flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to Pittsburgh

Have a flexible travel schedule? Discover the best time to fly to Pittsburgh 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 Pittsburgh

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

Currently, May is the cheapest month in which you can book a flight from New Windsor to Pittsburgh (average of $31). Flying from New Windsor to Pittsburgh in December is currently the most expensive (average of $65). 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 Pittsburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Airlines like Allegiant Air fly from New Windsor to Pittsburgh in about 21h 45m. The time it takes to get you to your destination can typically vary by up to . The distance from New Windsor to Pittsburgh is about 327 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Pittsburgh 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 Pittsburgh?

    Currently, May is the cheapest month in which you can book a flight from New Windsor to Pittsburgh (average of $31). Flying from New Windsor to Pittsburgh in December is currently the most expensive (average of $65). 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 Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Mars
Steubenville
Washington
Monroeville
Wexford
Belle Vernon

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Alternative routes for Stewart to Pittsburgh

See prices for flight routes from nearby airports that may be better suited for you.
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