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$106+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PIT
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
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 March 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/21. 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 6/55:55 pm
SWF
-
PIT
1 stop5h 16m
Multiple Airlines
Sat 6/69:13 pm
PIT
-
SWF
1 stop12h 25m
Multiple Airlines
Deal found 3/21$247
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 6/410:28 am
SWF
-
PIT
1 stop11h 59m
Multiple Airlines
Sat 6/69:13 pm
PIT
-
SWF
1 stop12h 25m
Multiple Airlines
Deal found 3/21$255
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/3011:45 am
SWF
-
PIT
1 stop12h 14m
Multiple Airlines
Sat 5/26:15 pm
PIT
-
SWF
1 stop16h 40m
Multiple Airlines
Deal found 3/20$280
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 5/2110:28 am
SWF
-
PIT
1 stop23h 09m
Multiple Airlines
Tue 5/265:49 pm
PIT
-
SWF
1 stop17h 36m
Multiple Airlines
Deal found 3/21$284
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Mon 6/15:53 pm
SWF
-
PIT
1 stop4h 58m
Multiple Airlines
Wed 6/38:15 pm
PIT
-
SWF
1 stop12h 43m
Multiple Airlines
Deal found 3/17$294
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Mon 7/1312:17 pm
SWF
-
PIT
1 stop24h 38m
Breeze Airways
Tue 7/215:49 pm
PIT
-
SWF
1 stop17h 36m
Breeze Airways
Deal found 3/18$295
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 6/1110:28 am
SWF
-
PIT
1 stop11h 59m
Multiple Airlines
Sun 6/1412:36 pm
PIT
-
SWF
1 stop5h 07m
Multiple Airlines
Deal found 3/20$301
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Thu 5/711:45 am
SWF
-
PIT
1 stop10h 42m
Multiple Airlines
Sun 5/108:15 pm
PIT
-
SWF
2 stops15h 22m
Multiple Airlines
Deal found 3/17$313
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Wed 7/1512:05 pm
SWF
-
PIT
1 stop28h 01m
Breeze Airways
Tue 7/215:49 pm
PIT
-
SWF
1 stop17h 36m
Breeze Airways
Deal found 3/18$317
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 5/1411:45 am
SWF
-
PIT
1 stop10h 42m
Multiple Airlines
Sat 5/168:15 pm
PIT
-
SWF
1 stop12h 43m
Multiple Airlines
Deal found 3/19$327

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 March 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(Kiwi.com)

One-way from

$106
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$233
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. 8% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 22, 2026.
Use the filters below to find and compare flights from New Windsor to Pittsburgh that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 6/5

5:55 pm-11:11 pm

1 stop5h 16m

Pittsburgh

Sat 6/6

9:13 pm-9:38 am

1 stop12h 25m

$247

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 4/30

11:45 am-11:59 pm

1 stop12h 14m

Pittsburgh

Sat 5/2

6:15 pm-10:55 am

1 stop16h 40m

$280

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Mon 6/1

5:53 pm-10:51 pm

1 stop4h 58m

Pittsburgh

Wed 6/3

8:15 pm-8:58 am

1 stop12h 43m

$294

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 6/11

10:28 am-10:27 pm

1 stop11h 59m

Pittsburgh

Sun 6/14

12:36 pm-5:43 pm

1 stop5h 07m

$301
Quickest round-trip

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 5/7

11:45 am-10:27 pm

1 stop10h 42m

Pittsburgh

Sun 5/10

12:36 pm-5:25 pm

1 stop4h 49m

$348

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 6/11

10:28 am-10:27 pm

1 stop11h 59m

Pittsburgh

Mon 6/15

11:33 am-6:38 pm

1 stop7h 05m

$360

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 6/18

10:28 am-8:27 pm

1 stop9h 59m

Pittsburgh

Sat 6/20

9:32 pm-9:38 am

1 stop12h 06m

$397

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 5/14

11:45 am-10:27 pm

1 stop10h 42m

Pittsburgh

Sun 5/17

12:36 pm-5:25 pm

1 stop4h 49m

$397

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 6/12

5:55 pm-11:11 pm

1 stop5h 16m

Pittsburgh

Sun 6/14

4:46 pm-8:49 am

2 stops16h 03m

$401

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 6/19

5:50 pm-11:11 pm

1 stop5h 21m

Pittsburgh

Sat 6/20

9:32 pm-9:38 am

1 stop12h 06m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 19 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub the most. FlightHub 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 February is currently the most expensive (average of $99). 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.

  • 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 February is currently the most expensive (average of $99). 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
Chester
Steubenville
Washington
Monroeville
Wexford
Belle Vernon

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