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Stewart

$120+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SWF
5月 26 — 6月 21
週二 5/26
週二 6/2
1 adult, Economy
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Cheap 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 4月 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
週五 6/58:15 pm
PIT
-
SWF
2 stops15h 10m
Multiple Airlines
週一 6/89:39 am
SWF
-
PIT
1 stop10h 58m
Multiple Airlines
Deal found 4/24$253
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
週五 9/259:12 pm
PIT
-
SWF
1 stop14h 27m
Multiple Airlines
週五 10/211:19 am
SWF
-
PIT
1 stop11h 43m
Multiple Airlines
Deal found 4/23$260
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
週二 9/85:49 pm
PIT
-
SWF
1 stop17h 50m
Multiple Airlines
週一 9/141:21 pm
SWF
-
PIT
1 stop5h 24m
Multiple Airlines
Deal found 4/23$270
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
週五 7/249:18 pm
PIT
-
SWF
1 stop20h 36m
Allegiant Air
週一 7/275:49 pm
SWF
-
PIT
1 stop4h 58m
Allegiant Air
Deal found 4/22$278
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
週五 5/88:15 pm
PIT
-
SWF
2 stops15h 10m
Multiple Airlines
週日 5/109:38 am
SWF
-
PIT
1 stop9h 32m
Multiple Airlines
Deal found 4/24$283
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
週三 8/195:23 pm
PIT
-
SWF
1 stop18h 47m
Multiple Airlines
週日 8/231:00 pm
SWF
-
PIT
1 stop27h 28m
Multiple Airlines
Deal found 4/24$286
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
週五 5/88:15 pm
PIT
-
SWF
2 stops15h 10m
Multiple Airlines
週六 7/44:13 pm
SWF
-
PIT
1 stop6h 12m
Multiple Airlines
Deal found 4/25$289
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
週三 6/38:15 pm
PIT
-
SWF
1 stop12h 43m
Multiple Airlines
週六 6/612:05 pm
SWF
-
PIT
2 stops35h 24m
Multiple Airlines
Deal found 4/24$297
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
週五 6/127:09 pm
PIT
-
SWF
2 stops16h 16m
Multiple Airlines
週一 6/155:55 pm
SWF
-
PIT
1 stop5h 16m
Multiple Airlines
Deal found 4/25$298
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
週二 5/265:49 pm
PIT
-
SWF
1 stop17h 36m
Multiple Airlines
週四 5/289:38 am
SWF
-
PIT
1 stop9h 42m
Multiple Airlines
Deal found 4/25$299
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
週二 5/265:49 pm
PIT
-
SWF
1 stop17h 36m
Multiple Airlines
週五 5/299:41 am
SWF
-
PIT
1 stop10h 58m
Multiple Airlines
Deal found 4/22$301

Find 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 4月 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$253
(Kiwi.com)

One-way from

$120
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$211
Provider with most accurate pricing for Pittsburgh-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-New Windsor Stewart flights.
Search Deals
From Pittsburgh to New Windsor Stewart
Search Deals
One-way flight from Pittsburgh to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($32 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 April 2026
Search Deals

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 4月 26, 2026.
Use the filters below to find and compare flights from Pittsburgh to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週五 6/5

8:15 pm-11:25 am

2 stops15h 10m

New Windsor Stewart

週一 6/8

9:39 am-8:37 pm

1 stop10h 58m

$253

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週三 7/8

6:54 pm-9:38 am

1 stop14h 44m

New Windsor Stewart

週六 7/11

6:44 pm-11:16 am

1 stop16h 32m

$307

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週五 7/10

9:18 pm-5:54 pm

1 stop20h 36m

New Windsor Stewart

週一 7/13

5:49 pm-10:47 pm

1 stop4h 58m

$316

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週一 8/3

11:33 am-6:51 pm

1 stop7h 18m

New Windsor Stewart

週六 8/8

12:05 pm-4:06 pm

1 stop28h 01m

$331

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週日 8/16

5:47 pm-11:37 am

1 stop17h 50m

New Windsor Stewart

週四 8/20

6:16 pm-11:37 am

1 stop17h 21m

$386

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週二 6/9

9:11 pm-11:25 am

2 stops14h 14m

New Windsor Stewart

週一 7/13

5:49 pm-10:47 pm

1 stop4h 58m

$395

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週一 6/8

11:33 am-6:36 pm

1 stop7h 03m

New Windsor Stewart

週一 6/15

5:55 pm-11:11 pm

1 stop5h 16m

$405
Quickest round-trip

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週一 5/25

11:38 am-6:56 pm

1 stop7h 18m

New Windsor Stewart

週一 6/1

5:53 pm-10:51 pm

1 stop4h 58m

$420

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週五 8/14

7:30 am-6:45 pm

1 stop11h 15m

New Windsor Stewart

週日 8/16

6:39 pm-11:37 am

1 stop16h 58m

$474

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

週五 6/19

11:33 am-6:38 pm

1 stop7h 05m

New Windsor Stewart

週日 6/21

6:33 pm-5:49 pm

2 stops23h 16m

$488

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 22 resultsSorted by cheapest first
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3

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 April.
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 Pittsburgh-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-New Windsor flight deals on Cheapflights vs. FlightHub >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 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 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.

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 7h 03m. 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.

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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