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Stewart

$100+ Cheap flights from Pittsburgh to New Windsor (PIT - 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SWF
Dec 17 — Dec 241
Wed 12/17
Wed 12/24
1 adult, Economy
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Cheap flight deals from Pittsburgh to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Stewart (SWF). 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 November 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$234
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$195
Provider with most accurate pricing for Pittsburgh-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Pittsburgh-New Windsor Stewart flights.
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From Pittsburgh to New Windsor Stewart
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One-way flight from Pittsburgh to New Windsor Stewart
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Highest demand for flights based on searches. 14% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Pittsburgh to Stewart

Cheapest flights from Pittsburgh to Stewart
Explore the most affordable flight options available from Pittsburgh to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/15. 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.
Thu 12/113:00 pmPIT - SWF
1 stop27h 40mMultiple Airlines
Fri 1/911:09 amSWF - PIT
1 stop12h 35mMultiple Airlines
Deal found 11/15$234
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 12/181:00 pmPIT - SWF
2 stops29h 06mMultiple Airlines
Mon 12/228:25 pmSWF - PIT
1 stop13h 33mMultiple Airlines
Deal found 11/14$316
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/178:01 pmPIT - SWF
1 stop14h 18mMultiple Airlines
Fri 12/196:56 pmSWF - PIT
1 stop15h 02mMultiple Airlines
Deal found 11/16$338
This Mytrip deal was found by Cheapflights users on 11/15. 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 Mytrip 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
Sat 12/209:45 amSWF - PIT
1 stop13h 34mAllegiant Air
Deal found 11/15$343
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/198:00 amPIT - SWF
1 stop10h 06mMultiple Airlines
Tue 12/2311:43 amSWF - PIT
1 stop11h 16mMultiple Airlines
Deal found 11/17$355
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/17:30 amPIT - SWF
1 stop12h 01mMultiple Airlines
Fri 12/512:24 pmSWF - PIT
1 stop19h 22mMultiple Airlines
Deal found 11/16$453
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/246:00 amPIT - SWF
1 stop10h 44mMultiple Airlines
Sat 12/278:45 pmSWF - PIT
1 stop26h 14mMultiple Airlines
Deal found 11/16$456
This Kiwi.com deal was found by Cheapflights users on 11/16. 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.
Fri 12/198:00 amPIT - SWF
1 stop8h 38mMultiple Airlines
Sun 12/216:28 pmSWF - PIT
2 stops28h 14mMultiple Airlines
Deal found 11/16$458
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 12/236:00 amPIT - SWF
1 stop10h 00mAllegiant Air
Wed 12/245:34 pmSWF - PIT
1 stop21h 45mAllegiant Air
Deal found 11/15$469
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/246:00 amPIT - SWF
1 stop10h 44mMultiple Airlines
Fri 12/2612:24 pmSWF - PIT
1 stop19h 22mMultiple Airlines
Deal found 11/16$490

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh 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 November 17, 2025.
Use the filters below to find and compare flights from Pittsburgh to New Windsor that are best for you.

Fly from

Pittsburgh

Fly to

Stewart

Route

Depart

Return

Price

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 12/11

3:00 pm-6:40 pm

1 stop27h 40m

New Windsor Stewart

Fri 1/9

11:09 am-11:44 pm

1 stop12h 35m

$234

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 12/18

1:00 pm-6:06 pm

2 stops29h 06m

New Windsor Stewart

Mon 12/22

8:25 pm-9:58 am

1 stop13h 33m

$316

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 12/17

8:01 pm-10:19 am

1 stop14h 18m

New Windsor Stewart

Fri 12/19

6:56 pm-9:58 am

1 stop15h 02m

$338

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 12/17

8:01 pm-10:19 am

1 stop14h 18m

New Windsor Stewart

Sat 12/20

9:45 am-11:19 pm

1 stop13h 34m

$344

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 12/19

8:00 am-6:06 pm

1 stop10h 06m

New Windsor Stewart

Tue 12/23

11:43 am-10:59 pm

1 stop11h 16m

$355

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 12/1

7:30 am-7:31 pm

1 stop12h 01m

New Windsor Stewart

Fri 12/5

12:24 pm-7:46 am

1 stop19h 22m

$453

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 12/24

6:00 am-4:44 pm

1 stop10h 44m

New Windsor Stewart

Sat 12/27

8:45 pm-10:59 pm

1 stop26h 14m

$456

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 12/19

8:00 am-4:38 pm

1 stop8h 38m

New Windsor Stewart

Sun 12/21

6:28 pm-10:42 pm

2 stops28h 14m

$458

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Tue 12/23

6:00 am-4:00 pm

1 stop10h 00m

New Windsor Stewart

Wed 12/24

5:34 pm-3:19 pm

1 stop21h 45m

$469

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 12/24

6:00 am-4:44 pm

1 stop10h 44m

New Windsor Stewart

Fri 12/26

12:24 pm-7:46 am

1 stop19h 22m

$490

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

Showing 1-10 of 22 results
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Compare providers for flights from Pittsburgh to Stewart

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 Pittsburgh to Stewart in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 Pittsburgh-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Pittsburgh-New Windsor flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Pittsburgh-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pittsburgh-New Windsor flights, Cheapflights users trust eDreams the most. eDreams 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 Pittsburgh-New Windsor 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 Pittsburgh to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Pittsburgh 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 Pittsburgh to New Windsor

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

Currently, April is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $42). Flying from Pittsburgh to New Windsor in January is currently the most expensive (average of $68). 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 PIT to SWF?

Find hourly flight availability from Pittsburgh 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 November 17, 2025.

It’s typically best to fly out from Pittsburgh to New Windsor in the morning. Doing so could potentially save you 79% on the flight price compared to flying in the evening, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Stewart. 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 Pittsburgh to New Windsor?

    Allegiant Air can get you from Pittsburgh to New Windsor in just under 14h 18m. Your travel time can differ by up to . The distance from Pittsburgh to New Windsor is about 327 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pittsburgh 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 Pittsburgh to New Windsor?

    Currently, April is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $42). Flying from Pittsburgh to New Windsor in January is currently the most expensive (average of $68). 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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