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Stewart

$192+ Cheap flights from Pensacola to New Windsor (PNS - 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SWF
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Pensacola to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) 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 August 18, 2025.

Round-trip from

$469
(Kiwi.com)

One-way from

$192
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$294
From Pensacola to New Windsor Stewart
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One-way flight from Pensacola to New Windsor Stewart
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Highest demand for flights based on searches. 9% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Pensacola to Stewart

Cheapest flights from Pensacola to Stewart
Explore the most affordable flight options available from Pensacola to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/117:10 pmPNS - SWF
2 stops15h 34mMultiple Airlines
Thu 9/1811:43 amSWF - PNS
1 stop7h 27mMultiple Airlines
Deal found 8/17$469
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/117:10 pmPNS - SWF
2 stops15h 34mMultiple Airlines
Sun 9/1411:43 amSWF - PNS
1 stop7h 27mMultiple Airlines
Deal found 8/16$498
This KAYAK deal was found by Cheapflights users on 8/16. 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.
Wed 8/2711:13 amPNS - SWF
2 stops30h 59mBreeze Airways
Tue 9/212:36 pmSWF - PNS
2 stops29h 28mBreeze Airways
Deal found 8/16$866
This KAYAK deal was found by Cheapflights users on 8/16. 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.
Wed 8/2711:13 amPNS - SWF
2 stops30h 59mBreeze Airways
Fri 9/512:24 pmSWF - PNS
3 stops29h 40mBreeze Airways
Deal found 8/16$880
This KAYAK deal was found by Cheapflights users on 8/16. 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.
Sat 8/3011:13 amPNS - SWF
2 stops30h 59mBreeze Airways
Tue 9/212:36 pmSWF - PNS
2 stops29h 28mBreeze Airways
Deal found 8/16$895
This KAYAK deal was found by Cheapflights users on 8/16. 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.
Sat 8/3011:13 amPNS - SWF
2 stops30h 59mBreeze Airways
Fri 9/512:24 pmSWF - PNS
3 stops29h 40mBreeze Airways
Deal found 8/16$910

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pensacola 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 August 18, 2025.
Use the filters below to find and compare flights from Pensacola to New Windsor that are best for you.

Fly from

Pensacola

Fly to

Stewart

Route

Depart

Return

Price

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Thu 9/11

7:10 pm-11:44 am

2 stops15h 34m

New Windsor Stewart

Thu 9/18

11:43 am-6:10 pm

1 stop7h 27m

$469

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Thu 9/11

7:10 pm-11:44 am

2 stops15h 34m

New Windsor Stewart

Sun 9/14

11:43 am-6:10 pm

1 stop7h 27m

$498

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sat 8/30

11:13 am-7:12 pm

2 stops30h 59m

New Windsor Stewart

Tue 9/2

12:36 pm-5:04 pm

2 stops29h 28m

$895

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sat 8/30

11:13 am-7:12 pm

2 stops30h 59m

New Windsor Stewart

Fri 9/5

12:24 pm-5:04 pm

3 stops29h 40m

$910

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 8/24

4:52 pm-4:46 pm

1 stop22h 54m

$192

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Tue 11/4

4:36 pm-12:42 pm

2 stops43h 06m

$195

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Tue 11/11

4:41 pm-12:42 pm

2 stops43h 01m

$200

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 9/7

7:10 pm-11:44 am

2 stops15h 34m

$244

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Fri 10/10

5:46 pm-4:55 pm

2 stops46h 09m

$259

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Tue 11/25

4:41 pm-11:27 am

1 stop17h 46m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 13 results
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Best time to book a flight from Pensacola to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Pensacola to New Windsor (average of $109). Flying from Pensacola to New Windsor in December is currently the most expensive (average of $202). 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 Pensacola 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 Pensacola to New Windsor?

    There are many flights that can get you from Pensacola to New Windsor in 30h 59m. Fly via Breeze Airways to get the fastest option. Airlines will cover a distance of 1053 mi.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Pensacola to New Windsor (average of $109). Flying from Pensacola to New Windsor in December is currently the most expensive (average of $202). 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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