$121+ Cheap flights from Pittsburgh to New Windsor (PIT - SWF)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SWF
Oct 9 — Oct 161
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh to Stewart 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 Pittsburgh to Stewart
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Cheapest flights from Pittsburgh to StewartExplore 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 September 9, 2026.
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 September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 12/48:54 pm -
1 stop14h 45m
Thu 12/106:49 pm -
1 stop24h 20m
Deal found 9/6![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 12/118:54 pm -
1 stop14h 45m
Sun 1/108:01 pm -
1 stop22h 36m
Deal found 9/7![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Tue 11/171:41 pm -
2 stops21h 58m
Thu 1/78:01 pm -
1 stop22h 36m
Deal found 9/5![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 12/37:13 pm -
1 stop16h 23m
Sun 12/66:49 pm -
1 stop24h 20m
Deal found 9/4![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/106:17 pm -
1 stop16h 46m
Sun 10/1811:53 am -
1 stop30h 55m
Deal found 9/8![Allegiant Air logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 12/38:15 am -
1 stop24h 37m
Sun 12/66:49 pm -
1 stop24h 20m
Deal found 9/7![Allegiant Air logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/68:54 pm -
1 stop14h 45m
Wed 11/1112:39 pm -
2 stops28h 53m
Deal found 9/8![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/31:41 pm -
2 stops21h 58m
Sun 11/812:00 pm -
1 stop30h 22m
Deal found 9/7![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 11/68:54 pm -
1 stop14h 45m
Fri 11/1311:09 am -
1 stop12h 02m
Deal found 9/6![Multiple Airlines logo]()
$339
Best flights from Pittsburgh to StewartDiscover carefully curated flight deals from Pittsburgh to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
Discover carefully curated flight deals from Pittsburgh to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 12/37:13 pm -
1 stop16h 23m
Sun 12/66:49 pm -
1 stop24h 20m
Deal found 9/4![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 12/38:15 am -
1 stop24h 37m
Sun 12/66:49 pm -
1 stop24h 20m
Deal found 9/7![Allegiant Air logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/68:54 pm -
1 stop14h 45m
Wed 11/1112:39 pm -
2 stops28h 53m
Deal found 9/8![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/98:54 pm -
1 stop14h 45m
Sat 10/1712:39 pm -
2 stops30h 17m
Deal found 9/8![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/106:17 pm -
1 stop16h 46m
Mon 10/1212:19 pm -
1 stop8h 52m
Deal found 9/8![Allegiant Air logo]()
$517
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/98:54 pm -
1 stop14h 45m
Sun 10/115:48 pm -
1 stop4h 39m
Deal found 9/8![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/12:32 pm -
2 stops21h 04m
Sun 10/47:09 pm -
1 stop22h 59m
Deal found 9/8![Multiple Airlines logo]()
$534
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/258:00 am -
1 stop4h 51m
Sun 9/2710:56 am -
2 stops33h 03m
Deal found 9/8![Multiple Airlines logo]()
$588
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/98:54 pm -
1 stop14h 45m
Mon 10/1212:19 pm -
1 stop8h 52m
Deal found 9/6![Multiple Airlines logo]()
$589
Last-minute flights from Pittsburgh to StewartDiscover last-minute flight deals from Pittsburgh to Stewart. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Stewart. Data last updated September 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/12:32 pm -
2 stops21h 04m
Mon 10/57:13 pm -
1 stop18h 34m
Deal found 9/8![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/28:54 pm -
1 stop14h 45m
Mon 10/57:13 pm -
1 stop18h 34m
Deal found 9/9![Multiple Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Sat 10/36:17 pm -
1 stop16h 41m
Sat 10/1012:39 pm -
2 stops21h 02m
Deal found 9/4![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/98:54 pm -
1 stop14h 45m
Sun 10/1811:53 am -
1 stop30h 55m
Deal found 9/6![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/106:17 pm -
1 stop16h 46m
Sun 10/1811:53 am -
1 stop30h 55m
Deal found 9/8![Allegiant Air logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/168:54 pm -
1 stop14h 45m
Sat 10/2412:39 pm -
2 stops30h 17m
Deal found 9/5![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/227:13 pm -
1 stop16h 23m
Thu 10/2910:38 am -
1 stop31h 04m
Deal found 9/7![Multiple Airlines logo]()
$376
One-way flights from Pittsburgh to StewartSearch for one-way flight options from Pittsburgh to Stewart. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
Search for one-way flight options from Pittsburgh to Stewart. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/36:17 pm -
1 stop16h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Allegiant Air logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/68:54 pm -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Breeze Airways logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 11/138:54 pm -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Breeze Airways logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 12/48:54 pm -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Breeze Airways logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/246:17 pm -
1 stop16h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Allegiant Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Sat 10/106:17 pm -
1 stop16h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Allegiant Air logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/308:54 pm -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Breeze Airways logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/176:17 pm -
1 stop16h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Allegiant Air logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/238:54 pm -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 11/171:41 pm -
2 stops21h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/168:54 pm -
1 stop14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Breeze Airways logo]()
$151
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 September 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Kiwi.com) |
One-way from | $121 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $222 |
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 7,457,451 searches. Data last updated September 9, 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
Cheapest round-trip
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Sat 10/24
6:17 pm-11:08 am
1 stop16h 51m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$138
Quickest round-trip
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Fri 10/23
8:54 pm-11:39 am
1 stop14h 45m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$146
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Sat 10/10
6:17 pm-11:03 am
1 stop16h 46m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$156
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Fri 10/2
8:54 pm-11:39 am
1 stop14h 45m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$163
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Sun 2/7
7:31 pm-10:57 am
1 stop15h 26m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$174
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Sun 11/22
4:37 pm-10:09 am
2 stops41h 32m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$225
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Thu 10/22
7:51 pm-11:36 am
2 stops15h 45m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Mon 10/19
7:38 pm-11:39 am
3 stops40h 01m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Sun 11/22
7:13 pm-11:36 am
1 stop16h 23m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$239
PittsburghNew Windsor
PIT Pittsburgh - SWF New Windsor Stewart
PITSWF
Pittsburgh
Sat 10/17
6:17 pm-6:24 pm
2 stops24h 07m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$249
Showing 1-10 of 20 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
PIT-SWF
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.
Traveling to a place near New Windsor?
Book flights to New Windsor if you plan to visit one of these locationsKingston
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