HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$105+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — SWF
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pennsylvania 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 Pennsylvania to Stewart

Keep the following information in mind while searching for Pennsylvania to Stewart flight deals. Data was last updated June 12, 2025.

Round-trip from

$218
(Mytrip)

One-way from

$105
(Mytrip)

Popular in

November

Cheapest in

August

Average price

$278
From Pennsylvania to New Windsor Stewart
Search Deals
One-way flight from Pennsylvania to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/10. 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.
Mon 9/223:41 pmPIT - SWF
1 stop18h 45mAllegiant Air
Thu 9/257:12 pmSWF - PIT
1 stop25h 59mAllegiant Air
Deal found 6/10$218
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Mon 6/306:20 amPHL - SWF
1 stop12h 51mMultiple Airlines
Fri 7/47:56 pmSWF - PHL
1 stop21h 04mMultiple Airlines
Deal found 6/11$228
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/173:47 pmPIT - SWF
1 stop25h 34mMultiple Airlines
Sun 7/206:42 pmSWF - PIT
1 stop26h 44mMultiple Airlines
Deal found 6/11$233
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/189:15 amMDT - SWF
1 stop24h 58mAllegiant Air
Wed 7/237:00 pmSWF - MDT
1 stop20h 46mAllegiant Air
Deal found 6/11$247
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/249:25 amIAD - SWF
1 stop25h 04mMultiple Airlines
Mon 7/286:11 pmSWF - IAD
3 stops22h 04mMultiple Airlines
Deal found 6/11$309
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sat 6/1411:56 amMDT - SWF
1 stop5h 02mMultiple Airlines
Mon 6/165:56 pmSWF - MDT
2 stops23h 52mMultiple Airlines
Deal found 6/10$555
This KAYAK deal was found by Cheapflights users on 6/11. 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 7/179:08 pmPIT - SWF
1 stop15h 40mBreeze Airways
Mon 7/211:28 pmSWF - PIT
1 stop19h 16mBreeze Airways
Deal found 6/11$602

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 June 12, 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

Mon 9/22

3:41 pm-10:26 am

1 stop18h 45m

New Windsor Stewart

Thu 9/25

7:12 pm-9:11 pm

1 stop25h 59m

$218

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Mon 6/30

6:20 am-7:11 pm

1 stop12h 51m

New Windsor Stewart

Fri 7/4

7:56 pm-5:00 pm

1 stop21h 04m

$228

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 7/17

3:47 pm-5:21 pm

1 stop25h 34m

New Windsor Stewart

Sun 7/20

6:42 pm-9:26 pm

1 stop26h 44m

$233

HarrisburgNew Windsor

MDT - SWF

MDTSWF

Harrisburg

Fri 7/18

9:15 am-10:13 am

1 stop24h 58m

New Windsor Stewart

Wed 7/23

7:00 pm-3:46 pm

1 stop20h 46m

$247

Washington, D.C.New Windsor

IAD - SWF

IADSWF

Washington, D.C. Dulles Intl

Thu 7/24

9:25 am-10:29 am

1 stop25h 04m

New Windsor Stewart

Mon 7/28

6:11 pm-4:15 pm

3 stops22h 04m

$309

AllentownNew Windsor

ABE - SWF

ABESWF

Allentown-Bethlehem

Wed 7/23

9:30 am-6:10 pm

1 stop8h 40m

New Windsor Stewart

Mon 7/28

11:19 am-10:02 pm

1 stop10h 43m

$433

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 7/17

9:08 pm-12:48 pm

1 stop15h 40m

New Windsor Stewart

Mon 7/21

1:28 pm-8:44 am

1 stop19h 16m

$602

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Mon 6/30

7:00 am-7:11 pm

1 stop12h 11m

$105

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 7/2

7:00 am-6:10 pm

1 stop11h 10m

$112

HarrisburgNew Windsor

MDT - SWF

MDTSWF

Harrisburg

Sun 8/24

4:53 pm-10:12 am

1 stop17h 19m

$121

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 18 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 $219). 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 June 12, 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 June 12, 2025.
Read through reviews of airlines operating flights from Pennsylvania to New Windsor, such as Breeze Airways and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

Food

6.7

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
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

Food

6.7

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
725 reviews
Breeze Airways
8.1
Very good
178 reviews

Entertainment

6.6

Crew

8.8

Overall

8.1

Comfort

8.2

Boarding

8.3

Food

6.7

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, Washington, D.C. Dulles Intl - New Windsor Stewart or Harrisburg - 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 $219). 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

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 Pennsylvania to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to John F Kennedy Intl flights
Los Angeles to Newark flights
Dallas/Fort Worth to Newark flights
O'Hare Intl to John F Kennedy Intl flights
San Francisco to John F Kennedy Intl flights
San Francisco to Newark flights
Los Angeles to LaGuardia flights
Atlanta to John F Kennedy Intl flights
Fort Lauderdale to LaGuardia flights
Atlanta to LaGuardia flights
O'Hare Intl to LaGuardia flights
Miami to John F Kennedy Intl flights
Fort Lauderdale to Newark flights
Hobby to LaGuardia flights
Atlanta to Newark flights
Ontario to John F Kennedy Intl flights
Miami to LaGuardia flights
Hobby to John F Kennedy Intl flights
Orlando to LaGuardia flights
Seattle to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
San Francisco to LaGuardia flights
Hobby to Newark flights
Miami to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
O'Hare Intl to Newark flights
Seattle to Newark flights
Orlando to Newark flights
Burbank to Newark flights
Santa Ana to Newark flights
Denver to LaGuardia flights
Tampa to Newark flights
Minneapolis to LaGuardia flights
George Bush Intcntl to Newark flights
Austin to Newark flights
Denver to John F Kennedy Intl flights
Tampa to John F Kennedy Intl flights
George Bush Intcntl to LaGuardia flights
San Diego to John F Kennedy Intl flights
George Bush Intcntl to John F Kennedy Intl flights
Sky Harbor Intl to John F Kennedy Intl flights
Austin to John F Kennedy Intl flights
Minneapolis to Newark flights
Raleigh to LaGuardia flights
Midway to Newark flights
Tampa to LaGuardia flights
Denver to Newark flights
Midway to John F Kennedy Intl 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.