HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pittsburgh

$105+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PIT
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Pittsburgh with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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 3/2012:11 pm
SWF
-
PIT
1 stop26h 31m
Multiple Airlines
Wed 3/2510:45 am
PIT
-
SWF
1 stop22h 54m
Multiple Airlines
Deal found 2/4$301
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 stop11h 57m
Multiple Airlines
Sun 5/105:15 pm
PIT
-
SWF
1 stop17h 40m
Multiple Airlines
Deal found 2/3$308
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 5/299:41 am
SWF
-
PIT
1 stop10h 58m
Multiple Airlines
Sun 5/315:15 pm
PIT
-
SWF
1 stop15h 36m
Multiple Airlines
Deal found 2/3$310
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 5/299:41 am
SWF
-
PIT
1 stop10h 58m
Allegiant Air
Mon 6/111:38 am
PIT
-
SWF
1 stop7h 18m
Allegiant Air
Deal found 2/5$319
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 6/129:39 am
SWF
-
PIT
1 stop10h 58m
Multiple Airlines
Sun 6/145:47 pm
PIT
-
SWF
1 stop17h 48m
Multiple Airlines
Deal found 2/2$365
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 6/59:39 am
SWF
-
PIT
1 stop10h 58m
Multiple Airlines
Sun 6/75:47 pm
PIT
-
SWF
1 stop17h 48m
Multiple Airlines
Deal found 2/4$376
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/611:09 am
SWF
-
PIT
1 stop12h 35m
Multiple Airlines
Sun 2/84:29 pm
PIT
-
SWF
1 stop26h 14m
Multiple Airlines
Deal found 2/2$412
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 6/1810:28 am
SWF
-
PIT
1 stop13h 14m
Multiple Airlines
Mon 6/2211:33 am
PIT
-
SWF
1 stop7h 05m
Multiple Airlines
Deal found 2/4$440
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 7/44:13 pm
SWF
-
PIT
1 stop6h 12m
Allegiant Air
Mon 7/1311:33 am
PIT
-
SWF
1 stop7h 18m
Allegiant Air
Deal found 2/3$444

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$301
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$194
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. 11% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 5, 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

Fri 3/20

12:11 pm-2:42 pm

1 stop26h 31m

Pittsburgh

Wed 3/25

10:45 am-9:39 am

1 stop22h 54m

$301

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 5/7

11:45 am-11:42 pm

1 stop11h 57m

Pittsburgh

Sun 5/10

5:15 pm-10:55 am

1 stop17h 40m

$308

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 5/29

9:41 am-8:39 pm

1 stop10h 58m

Pittsburgh

Sun 5/31

5:15 pm-8:51 am

1 stop15h 36m

$310

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 5/29

9:41 am-8:39 pm

1 stop10h 58m

Pittsburgh

Mon 6/1

11:38 am-6:56 pm

1 stop7h 18m

$319

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 6/12

9:39 am-8:37 pm

1 stop10h 58m

Pittsburgh

Sun 6/14

5:47 pm-11:35 am

1 stop17h 48m

$365

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 6/5

9:39 am-8:37 pm

1 stop10h 58m

Pittsburgh

Sun 6/7

5:15 pm-8:49 am

1 stop15h 34m

$408

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 6/18

10:28 am-11:42 pm

1 stop13h 14m

Pittsburgh

Mon 6/22

11:33 am-6:38 pm

1 stop7h 05m

$440

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Sat 7/4

4:13 pm-10:25 pm

1 stop6h 12m

Pittsburgh

Mon 7/13

11:33 am-6:51 pm

1 stop7h 18m

$444

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Thu 5/21

10:28 am-11:42 pm

1 stop13h 14m

Pittsburgh

Mon 5/25

11:38 am-6:56 pm

1 stop7h 18m

$449

New WindsorPittsburgh

SWF - PIT

SWFPIT

New Windsor Stewart

Fri 6/19

9:39 am-8:37 pm

1 stop10h 58m

Pittsburgh

Wed 7/1

5:29 pm-8:58 am

1 stop15h 29m

$474

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 18 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 February.
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 January is currently the most expensive (average of $81). 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 10h 58m. 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 January is currently the most expensive (average of $81). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Pittsburgh

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Reagan-National flights
Newark to Dulles Intl flights
Buffalo to Newark flights
Buffalo to LaGuardia flights
Buffalo to John F Kennedy Intl flights
John F Kennedy Intl to Dulles Intl flights
LaGuardia to Dulles Intl flights
John F Kennedy Intl to Reagan-National flights
John F Kennedy Intl to Pittsburgh flights
Newark to Pittsburgh flights
Rochester to John F Kennedy Intl flights
Syracuse to John F Kennedy Intl flights
Rochester to Newark flights
Newark to Reagan-National flights
LaGuardia to Pittsburgh flights
Rochester to LaGuardia flights
Syracuse to LaGuardia flights
Rochester to Dulles Intl flights
Syracuse to Newark flights
Rochester to Reagan-National flights
Syracuse to Dulles Intl flights
Syracuse to Reagan-National flights
Albany to Dulles Intl flights
Buffalo to Reagan-National flights
Buffalo to Philadelphia flights
Albany to Reagan-National flights
Buffalo to Dulles Intl flights
White Plains to Dulles Intl flights
John F Kennedy Intl to Philadelphia flights
Rochester to Philadelphia flights
Syracuse to Philadelphia flights
Ithaca to Dulles Intl flights
White Plains to Reagan-National flights
Ithaca to John F Kennedy Intl flights
LaGuardia to Philadelphia flights
Albany to Pittsburgh flights
Newark to Philadelphia flights
Albany to Philadelphia flights
Albany to John F Kennedy Intl flights
Albany to LaGuardia flights
Albany to Newark flights
Ithaca to LaGuardia flights
White Plains to Pittsburgh flights
Newark to Harrisburg flights
Ithaca to Newark flights
Newark to State College flights
Syracuse to Pittsburgh flights
LaGuardia to Harrisburg flights
Stewart to Philadelphia flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.