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Stewart

$103+ Cheap flights from Philadelphia to New Windsor (PHL - 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — SWF
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Philadelphia to Stewart

Cheapest flights from Philadelphia to Stewart
Explore the most affordable flight options available from Philadelphia to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:00 pmPHL - SWF
1 stop13h 03mMultiple Airlines
Fri 12/1912:24 pmSWF - PHL
2 stops20h 43mMultiple Airlines
Deal found 12/11$490
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:00 pmPHL - SWF
1 stop13h 03mMultiple Airlines
Sat 12/209:45 amSWF - PHL
1 stop11h 02mMultiple Airlines
Deal found 12/11$520
This Mytrip deal was found by Cheapflights users on 12/10. 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.
Thu 12/258:54 pmPHL - SWF
1 stop14h 13mMultiple Airlines
Mon 12/2911:37 amSWF - PHL
1 stop11h 40mMultiple Airlines
Deal found 12/10$791
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Sun 12/2810:00 pmPHL - SWF
2 stops13h 44mMultiple Airlines
Tue 12/3011:43 amSWF - PHL
1 stop12h 13mMultiple Airlines
Deal found 12/9$863
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Sun 12/2110:00 pmPHL - SWF
2 stops13h 44mMultiple Airlines
Tue 12/2311:43 amSWF - PHL
1 stop13h 05mMultiple Airlines
Deal found 12/9$1,066

Find flight deals from Philadelphia to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Philadelphia (PHL) 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$174
(Mytrip)

One-way from

$103
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$554
Provider with most accurate pricing for Philadelphia-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Philadelphia-New Windsor Stewart flights.
Search Deals
From Philadelphia to New Windsor Stewart
Search Deals
One-way flight from Philadelphia to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($102 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Philadelphia 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 December 12, 2025.
Use the filters below to find and compare flights from Philadelphia to New Windsor that are best for you.

Fly from

Philadelphia

Fly to

Stewart

Route

Depart

Return

Price

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 1/8

6:11 pm-10:19 am

1 stop16h 08m

New Windsor Stewart

Mon 1/12

11:09 am-11:50 pm

1 stop12h 41m

$174

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 1/15

8:43 pm-11:31 am

2 stops14h 48m

New Windsor Stewart

Sun 1/18

12:13 pm-7:48 pm

1 stop7h 35m

$520

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 12/25

8:54 pm-11:07 am

1 stop14h 13m

New Windsor Stewart

Mon 12/29

11:37 am-11:17 pm

1 stop11h 40m

$791

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Fri 12/26

7:18 pm-11:03 am

2 stops39h 45m

New Windsor Stewart

Tue 12/30

11:43 am-8:39 pm

1 stop8h 56m

$791

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sun 12/28

10:00 pm-11:44 am

2 stops13h 44m

New Windsor Stewart

Tue 12/30

11:43 am-11:56 pm

1 stop12h 13m

$863

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sun 12/21

10:00 pm-11:44 am

2 stops13h 44m

New Windsor Stewart

Tue 12/23

11:43 am-12:48 am

1 stop13h 05m

$1,066

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sun 1/25

3:34 pm-10:19 am

1 stop18h 45m

$103

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Sat 1/10

4:03 pm-9:58 am

1 stop17h 55m

$109

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Thu 1/15

7:12 pm-10:19 am

2 stops15h 07m

$116

PhiladelphiaNew Windsor

PHL - SWF

PHLSWF

Philadelphia

Wed 1/28

7:04 pm-10:19 am

2 stops39h 15m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 15 results
1
2

Compare providers for flights from Philadelphia 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 Philadelphia to Stewart in December.
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 Philadelphia-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Philadelphia-New Windsor flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Philadelphia-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Philadelphia-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 Philadelphia-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 Philadelphia to Stewart

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

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

Currently, May is the cheapest month in which you can book a flight from Philadelphia to New Windsor (average of $155). Flying from Philadelphia to New Windsor in October is currently the most expensive (average of $496). 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.

Related info for your journey

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

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Philadelphia to New Windsor (average of $155). Flying from Philadelphia to New Windsor in October is currently the most expensive (average of $496). 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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