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Pensacola

$126+ Cheap flights from New Windsor to Pensacola (SWF - PNS)

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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PNS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Stewart to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Pensacola (PNS). 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 11, 2025.

Round-trip from

$308
(Kiwi.com)

One-way from

$126
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$338
From New Windsor Stewart to Pensacola
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One-way flight from New Windsor Stewart to Pensacola
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Highest demand for flights based on searches. 8% potential increase in price ($35 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 September 2025
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Find flight deals from Stewart to Pensacola

Cheapest flights from Stewart to Pensacola
Explore the most affordable flight options available from Stewart to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

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.
Thu 10/911:43 amSWF - PNS
1 stop7h 32mMultiple Airlines
Thu 10/164:36 pmPNS - SWF
1 stop17h 05mMultiple Airlines
Deal found 9/9$308
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.
Thu 11/611:43 amSWF - PNS
1 stop7h 11mMultiple Airlines
Thu 11/134:41 pmPNS - SWF
1 stop16h 30mMultiple Airlines
Deal found 9/9$384
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Thu 11/2011:43 amSWF - PNS
1 stop7h 11mMultiple Airlines
Wed 11/266:49 pmPNS - SWF
1 stop15h 14mMultiple Airlines
Deal found 9/11$393
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sun 11/2311:43 amSWF - PNS
1 stop7h 11mMultiple Airlines
Fri 11/287:54 pmPNS - SWF
1 stop13h 52mMultiple Airlines
Deal found 9/11$618
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.
Mon 12/228:25 pmSWF - PNS
1 stop20h 11mMultiple Airlines
Mon 12/297:54 pmPNS - SWF
2 stops20h 44mMultiple Airlines
Deal found 9/9$636
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2111:12 amSWF - PNS
1 stop22h 45mMultiple Airlines
Sat 11/296:49 pmPNS - SWF
1 stop24h 02mMultiple Airlines
Deal found 9/10$718
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 12/209:45 amSWF - PNS
2 stops27h 49mMultiple Airlines
Sun 12/284:41 pmPNS - SWF
1 stop17h 06mMultiple Airlines
Deal found 9/9$727

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Pensacola 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 September 11, 2025.
Use the filters below to find and compare flights from New Windsor to Pensacola that are best for you.

Fly from

Stewart

Fly to

Pensacola

Route

Depart

Return

Price

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 10/9

11:43 am-6:15 pm

1 stop7h 32m

Pensacola

Thu 10/16

4:36 pm-10:41 am

1 stop17h 05m

$308

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 11/6

11:43 am-5:54 pm

1 stop7h 11m

Pensacola

Thu 11/13

4:41 pm-10:11 am

1 stop16h 30m

$384

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 11/20

11:43 am-5:54 pm

1 stop7h 11m

Pensacola

Wed 11/26

6:49 pm-11:03 am

1 stop15h 14m

$393

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Sun 11/23

11:43 am-5:54 pm

1 stop7h 11m

Pensacola

Fri 11/28

7:54 pm-10:46 am

1 stop13h 52m

$618

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/22

8:25 pm-3:36 pm

1 stop20h 11m

Pensacola

Mon 12/29

7:54 pm-5:38 pm

2 stops20h 44m

$636

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Fri 11/21

11:12 am-8:57 am

1 stop22h 45m

Pensacola

Sat 11/29

6:49 pm-7:51 pm

1 stop24h 02m

$718

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Sat 12/20

9:45 am-12:34 pm

2 stops27h 49m

Pensacola

Sun 12/28

4:41 pm-10:47 am

1 stop17h 06m

$727

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/15

12:27 pm-3:36 pm

1 stop28h 09m

$126

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Fri 10/3

12:11 pm-3:39 pm

1 stop28h 28m

$129

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Sun 9/28

7:12 pm-2:55 pm

1 stop20h 43m

$172

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 15 results
1
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Best time to book a flight from Stewart to Pensacola

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

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

Currently, September is the cheapest month in which you can book a flight from New Windsor to Pensacola (average of $303). Flying from New Windsor to Pensacola in March is currently the most expensive (average of $415). 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 Stewart to Pensacola. 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 Stewart to Pensacola that include hotel bookings?

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from New Windsor to Pensacola (average of $303). Flying from New Windsor to Pensacola in March is currently the most expensive (average of $415). 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 Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Gulf Breeze
Navarre
Foley
Perdido Key
Navarre Beach
Warrington

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