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$99+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PIT
feb. 14 — feb. 211
sáb. 2/14
sáb. 2/21
1 adult, Economy
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Cheap 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 enero 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$335
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$199
Provider with most accurate pricing for New Windsor Stewart-Pittsburgh flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Pittsburgh flights.
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From New Windsor Stewart to Pittsburgh
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One-way flight from New Windsor Stewart to Pittsburgh
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Highest demand for flights based on searches. 10% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 enero 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
lun. 1/2611:09 am
SWF
-
PIT
1 stop22h 31m
Multiple Airlines
dom. 3/153:47 pm
PIT
-
SWF
1 stop17h 15m
Multiple Airlines
Deal found 1/15$293
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
vie. 1/3011:09 am
SWF
-
PIT
1 stop22h 31m
Multiple Airlines
mar. 2/36:15 pm
PIT
-
SWF
2 stops47h 44m
Multiple Airlines
Deal found 1/15$328
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
vie. 1/2311:09 am
SWF
-
PIT
1 stop12h 35m
Multiple Airlines
dom. 1/255:50 pm
PIT
-
SWF
1 stop16h 29m
Multiple Airlines
Deal found 1/15$331
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
dom. 6/79:38 am
SWF
-
PIT
1 stop13h 51m
Multiple Airlines
jue. 6/115:47 pm
PIT
-
SWF
1 stop17h 48m
Multiple Airlines
Deal found 1/14$365
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
jue. 1/2912:13 pm
SWF
-
PIT
1 stop10h 54m
Multiple Airlines
dom. 2/16:15 pm
PIT
-
SWF
1 stop16h 04m
Multiple Airlines
Deal found 1/15$378
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
dom. 6/76:33 pm
SWF
-
PIT
1 stop22h 13m
Multiple Airlines
dom. 6/145:47 pm
PIT
-
SWF
1 stop17h 48m
Multiple Airlines
Deal found 1/14$436
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
dom. 6/78:04 pm
SWF
-
PIT
1 stop27h 34m
Allegiant Air
vie. 6/1211:33 am
PIT
-
SWF
1 stop7h 03m
Allegiant Air
Deal found 1/14$444
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
dom. 3/111:48 am
SWF
-
PIT
1 stop11h 37m
Multiple Airlines
sáb. 3/75:45 pm
PIT
-
SWF
1 stop16h 23m
Multiple Airlines
Deal found 1/14$513
This Booking.com deal was found by Cheapflights users on 1/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/2912:05 pm
SWF
-
PIT
2 stops21h 28m
Breeze Airways
dom. 8/305:47 pm
PIT
-
SWF
1 stop17h 48m
Breeze Airways
Deal found 1/15$537
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
jue. 4/911:45 am
SWF
-
PIT
1 stop11h 29m
Multiple Airlines
dom. 4/125:45 am
PIT
-
SWF
2 stops11h 40m
Multiple Airlines
Deal found 1/14$542
This Booking.com deal was found by Cheapflights users on 1/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/312:05 pm
SWF
-
PIT
2 stops20h 28m
Breeze Airways
dom. 6/75:47 pm
PIT
-
SWF
1 stop17h 48m
Breeze Airways
Deal found 1/14$555

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 enero 15, 2026.
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

lun. 1/26

11:09 am-9:40 am

1 stop22h 31m

Pittsburgh

dom. 3/15

3:47 pm-9:02 am

1 stop17h 15m

$293

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

vie. 1/30

11:09 am-9:40 am

1 stop22h 31m

Pittsburgh

mar. 2/3

6:15 pm-5:59 pm

2 stops47h 44m

$328

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

dom. 6/7

9:38 am-11:29 pm

1 stop13h 51m

Pittsburgh

jue. 6/11

5:47 pm-11:35 am

1 stop17h 48m

$365

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

jue. 1/29

12:13 pm-11:07 pm

1 stop10h 54m

Pittsburgh

dom. 2/1

6:15 pm-10:19 am

1 stop16h 04m

$378

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

dom. 6/7

6:33 pm-4:46 pm

1 stop22h 13m

Pittsburgh

dom. 6/14

5:47 pm-11:35 am

1 stop17h 48m

$436

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

dom. 6/7

8:04 pm-11:38 pm

1 stop27h 34m

Pittsburgh

vie. 6/12

11:33 am-6:36 pm

1 stop7h 03m

$444

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

dom. 3/1

11:48 am-11:25 pm

1 stop11h 37m

Pittsburgh

sáb. 3/7

5:45 pm-10:08 am

1 stop16h 23m

$513

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

jue. 4/9

11:45 am-11:14 pm

1 stop11h 29m

Pittsburgh

dom. 4/12

5:45 am-5:25 pm

2 stops11h 40m

$542

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

mié. 6/3

12:05 pm-8:33 am

2 stops20h 28m

Pittsburgh

dom. 6/7

5:47 pm-11:35 am

1 stop17h 48m

$555

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

sáb. 6/6

12:05 pm-8:33 am

2 stops20h 28m

Pittsburgh

dom. 6/7

5:47 pm-11:35 am

1 stop17h 48m

$620

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 21 results
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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 January.
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 January is currently the most expensive (average of $80). 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 January is currently the most expensive (average of $80). 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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