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$144+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PNS
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$221
(Mytrip)

One-way from

$144
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$408
Provider with most accurate pricing for New Windsor Stewart-Pensacola flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Pensacola flights.
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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 ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This Mytrip deal was found by Cheapflights users on 10/28. 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 12/512:27 pmSWF - PNS
1 stop6h 47mMultiple Airlines
Sun 12/77:09 pmPNS - SWF
1 stop15h 28mMultiple Airlines
Deal found 10/28$221
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:56 pmSWF - PNS
1 stop24h 18mMultiple Airlines
Thu 12/257:09 pmPNS - SWF
1 stop14h 58mMultiple Airlines
Deal found 10/27$326
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/312:01 pmSWF - PNS
1 stop8h 10mMultiple Airlines
Thu 11/138:16 pmPNS - SWF
1 stop12h 55mMultiple Airlines
Deal found 10/28$328
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 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 stop17h 38mMultiple Airlines
Thu 12/257:09 pmPNS - SWF
1 stop14h 58mMultiple Airlines
Deal found 10/27$334
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:28 pmSWF - PNS
2 stops24h 46mMultiple Airlines
Thu 12/257:09 pmPNS - SWF
1 stop14h 58mMultiple Airlines
Deal found 10/27$349
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/711:31 amSWF - PNS
1 stop8h 40mMultiple Airlines
Thu 11/138:16 pmPNS - SWF
1 stop12h 55mMultiple Airlines
Deal found 10/28$362
This Mytrip deal was found by Cheapflights users on 10/26. 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 11/711:31 amSWF - PNS
1 stop8h 40mMultiple Airlines
Sun 11/98:16 pmPNS - SWF
1 stop13h 55mMultiple Airlines
Deal found 10/26$371
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 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 stop17h 38mMultiple Airlines
Sun 12/287:09 pmPNS - SWF
1 stop14h 38mMultiple Airlines
Deal found 10/27$372
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Wed 11/2612:17 pmSWF - PNS
1 stop7h 54mMultiple Airlines
Sat 11/298:16 pmPNS - SWF
1 stop12h 06mMultiple Airlines
Deal found 10/26$419
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/287:09 pmPNS - SWF
1 stop14h 38mMultiple Airlines
Deal found 10/26$436

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 October 28, 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

Fri 12/5

12:27 pm-6:14 pm

1 stop6h 47m

Pensacola

Sun 12/7

7:09 pm-11:37 am

1 stop15h 28m

$221

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Fri 12/19

6:56 pm-6:14 pm

1 stop24h 18m

Pensacola

Thu 12/25

7:09 pm-11:07 am

1 stop14h 58m

$326

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 11/3

12:01 pm-7:11 pm

1 stop8h 10m

Pensacola

Thu 11/13

8:16 pm-10:11 am

1 stop12h 55m

$328

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/22

8:25 pm-1:03 pm

1 stop17h 38m

Pensacola

Thu 12/25

7:09 pm-11:07 am

1 stop14h 58m

$334

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Sun 12/21

6:28 pm-6:14 pm

2 stops24h 46m

Pensacola

Thu 12/25

7:09 pm-11:07 am

1 stop14h 58m

$349

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Fri 11/7

11:31 am-7:11 pm

1 stop8h 40m

Pensacola

Thu 11/13

8:16 pm-10:11 am

1 stop12h 55m

$362

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Fri 11/7

11:31 am-7:11 pm

1 stop8h 40m

Pensacola

Sun 11/9

8:16 pm-11:11 am

1 stop13h 55m

$371

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/22

8:25 pm-1:03 pm

1 stop17h 38m

Pensacola

Sun 12/28

7:09 pm-10:47 am

1 stop14h 38m

$372

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Wed 11/26

12:17 pm-7:11 pm

1 stop7h 54m

Pensacola

Sat 11/29

8:16 pm-9:22 am

1 stop12h 06m

$419

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Sat 12/20

9:45 am-12:34 pm

2 stops27h 49m

Pensacola

Sun 12/28

7:09 pm-10:47 am

1 stop14h 38m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 16 results
1
2

Compare providers for flights from Stewart to Pensacola

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 Stewart to Pensacola in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*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 New Windsor-Pensacola flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Pensacola flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New Windsor-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Pensacola 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 New Windsor-Pensacola 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 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, March is the cheapest month in which you can book a flight from New Windsor to Pensacola (average of $89). Flying from New Windsor to Pensacola in April is currently the most expensive (average of $200). 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, March is the cheapest month in which you can book a flight from New Windsor to Pensacola (average of $89). Flying from New Windsor to Pensacola in April is currently the most expensive (average of $200). 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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