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Stewart

$103+ Cheap flights from Pennsylvania to New Windsor (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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — SWF
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap flight deals from Pennsylvania to Stewart

Keep the following information in mind while searching for Pennsylvania to Stewart flight deals. Data was last updated April 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(Mytrip)

One-way from

$103
(Mytrip)

Popular in

November

Cheapest in

August

Average price

$285
Provider with most accurate pricing for Philadelphia-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Philadelphia-New York (NYC) flights.
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From Pennsylvania to New Windsor Stewart
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One-way flight from Pennsylvania to New Windsor Stewart
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Highest demand for flights based on searches. 23% potential increase in price ($100 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Pennsylvania to Stewart

Cheapest flights from Pennsylvania to Stewart
Explore the most affordable flight options available from Pennsylvania to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2025.

This Mytrip deal was found by Cheapflights users on 4/29. 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.
Fri 5/3012:31 pmPIT - SWF
1 stop24h 31mMultiple Airlines
Mon 6/26:07 pmSWF - PIT
1 stop24h 11mMultiple Airlines
Deal found 4/29$226
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Fri 5/239:29 pmPIT - SWF
1 stop12h 44mAllegiant Air
Sun 5/256:09 pmSWF - PIT
1 stop5h 12mAllegiant Air
Deal found 4/28$242
This Mytrip deal was found by Cheapflights users on 4/27. 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.
Thu 6/269:21 amIAD - SWF
1 stop25h 10mMultiple Airlines
Fri 6/278:01 pmSWF - IAD
2 stops24h 51mMultiple Airlines
Deal found 4/27$308
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Fri 7/46:20 amPHL - SWF
1 stop12h 46mMultiple Airlines
Mon 7/76:11 pmSWF - PHL
2 stops28h 22mMultiple Airlines
Deal found 4/29$333
This KAYAK deal was found by Cheapflights users on 4/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/129:08 pmPIT - SWF
1 stop15h 40mBreeze Airways
Mon 6/161:28 pmSWF - PIT
1 stop19h 16mBreeze Airways
Deal found 4/29$599

Cheapflights Fare Finder

Customize your flight search to find flights from Pennsylvania 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 April 30, 2025.
Use the filters below to find and compare flights from Pennsylvania to New Windsor that are best for you.

Fly from

Pennsylvania

Fly to

Stewart

Route

Depart

Return

Price

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 5/30

12:31 pm-1:02 pm

1 stop24h 31m

New Windsor Stewart

Mon 6/2

6:07 pm-6:18 pm

1 stop24h 11m

$226

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 5/23

9:29 pm-10:13 am

1 stop12h 44m

New Windsor Stewart

Sun 5/25

6:09 pm-11:21 pm

1 stop5h 12m

$242

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Fri 7/4

6:20 am-7:06 pm

1 stop12h 46m

New Windsor Stewart

Mon 7/7

6:11 pm-10:33 pm

2 stops28h 22m

$333

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 5/30

9:05 pm-1:02 pm

2 stops15h 57m

New Windsor Stewart

Sun 6/1

6:06 pm-4:15 pm

3 stops22h 09m

$370

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 6/12

9:08 pm-12:48 pm

1 stop15h 40m

New Windsor Stewart

Mon 6/16

1:28 pm-8:44 am

1 stop19h 16m

$599

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 5/30

12:31 pm-1:02 pm

1 stop24h 31m

$106

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 5/23

9:29 pm-10:13 am

1 stop12h 44m

$111

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Mon 5/12

6:00 am-7:49 pm

1 stop13h 49m

$152

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Fri 6/27

4:54 pm-10:11 am

2 stops17h 17m

$179

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 5/8

8:25 am-9:11 am

3 stops24h 46m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 11 results
1
2

Best time to book a flight from Pennsylvania to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Pennsylvania to New Windsor (average of $109). Flying from Pennsylvania to New Windsor in August is currently the most expensive (average of $223). 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 PA to SWF?

Find hourly flight availability from Pennsylvania 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 April 30, 2025.

When flying from Pennsylvania to New Windsor, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Stewart. Reviews last updated April 30, 2025.
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Entertainment

6.6

Overall

8.1

Food

6.7

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Entertainment

6.6

Overall

8.1

Food

6.7

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.3
Good
734 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Entertainment

6.6

Overall

8.1

Food

6.7

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Pennsylvania to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Pennsylvania?

    Most people fly into New Windsor Stewart (SWF) if they book a flight to New Windsor from Pennsylvania. Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

  • What are the most popular routes from Pennsylvania to New Windsor?

    When deciding which route to take from Pennsylvania to New Windsor consider Pittsburgh - New Windsor Stewart, Philadelphia - New Windsor Stewart or Washington, D.C. Dulles Intl - New Windsor Stewart as they are the most popular.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Pennsylvania to New Windsor (average of $109). Flying from Pennsylvania to New Windsor in August is currently the most expensive (average of $223). 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 Pennsylvania?

Book flights to Pennsylvania if you plan to visit one of these locations
Kingston

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