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Pensacola

$138+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PNS
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/2611:48 am
SWF
-
PNS
1 stop6h 54m
Multiple Airlines
Sun 3/16:37 pm
PNS
-
SWF
1 stop14h 36m
Multiple Airlines
Deal found 1/25$283
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 6/1312:05 pm
SWF
-
PNS
2 stops21h 06m
Multiple Airlines
Wed 6/171:47 pm
PNS
-
SWF
1 stop18h 51m
Multiple Airlines
Deal found 1/26$352
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 4/2311:48 am
SWF
-
PNS
1 stop10h 33m
Multiple Airlines
Sun 4/266:00 am
PNS
-
SWF
2 stops28h 31m
Multiple Airlines
Deal found 1/25$379
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 6/149:38 am
SWF
-
PNS
1 stop12h 43m
Multiple Airlines
Wed 6/171:47 pm
PNS
-
SWF
1 stop18h 51m
Multiple Airlines
Deal found 1/26$433
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 7/239:38 am
SWF
-
PNS
1 stop12h 56m
Multiple Airlines
Sun 7/267:38 pm
PNS
-
SWF
2 stops14h 57m
Multiple Airlines
Deal found 1/27$436
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 1/2612:11 pm
SWF
-
PNS
2 stops29h 26m
Multiple Airlines
Sun 2/14:03 pm
PNS
-
SWF
1 stop17h 16m
Multiple Airlines
Deal found 1/25$497
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 6/149:38 am
SWF
-
PNS
1 stop12h 43m
Multiple Airlines
Thu 6/187:38 pm
PNS
-
SWF
2 stops14h 57m
Multiple Airlines
Deal found 1/26$534
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 6/149:38 am
SWF
-
PNS
1 stop12h 43m
Multiple Airlines
Sun 6/217:38 pm
PNS
-
SWF
2 stops14h 57m
Multiple Airlines
Deal found 1/26$536
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 6/259:38 am
SWF
-
PNS
1 stop12h 56m
Multiple Airlines
Sat 7/41:47 pm
PNS
-
SWF
1 stop18h 51m
Multiple Airlines
Deal found 1/26$566
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 6/259:38 am
SWF
-
PNS
1 stop12h 56m
Multiple Airlines
Sun 7/57:38 pm
PNS
-
SWF
2 stops14h 57m
Multiple Airlines
Deal found 1/26$680
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 7/29:38 am
SWF
-
PNS
1 stop12h 56m
Multiple Airlines
Mon 7/66:00 am
PNS
-
SWF
1 stop28h 08m
Multiple Airlines
Deal found 1/24$712

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$283
(Kiwi.com)

One-way from

$138
(Kiwi.com)

Popular in

April

Cheapest in

August

Average price

$359
Provider with most accurate pricing for New Windsor Stewart-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Pensacola flights.
Search Deals
From New Windsor Stewart to Pensacola
Search Deals
One-way flight from New Windsor Stewart to Pensacola
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 27, 2026.
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 2/26

11:48 am-5:42 pm

1 stop6h 54m

Pensacola

Sun 3/1

6:37 pm-10:13 am

1 stop14h 36m

$283

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 4/23

11:48 am-9:21 pm

1 stop10h 33m

Pensacola

Sun 4/26

6:00 am-11:31 am

2 stops28h 31m

$379

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 2/26

11:52 am-3:54 pm

1 stop29h 02m

$138

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 4/9

11:48 am-9:14 pm

1 stop10h 26m

$149

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Fri 2/6

7:33 pm-4:37 pm

1 stop22h 04m

$180

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 2/2

12:11 pm-4:37 pm

2 stops29h 26m

$182

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 2/5

10:48 am-2:32 pm

1 stop28h 44m

$262

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Thu 2/12

11:48 am-5:42 pm

1 stop30h 54m

$300

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Sat 2/14

7:29 pm-7:35 am

1 stop13h 06m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Pensacola flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $98). Flying from New Windsor to Pensacola in January is currently the most expensive (average of $201). 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 $98). Flying from New Windsor to Pensacola in January is currently the most expensive (average of $201). 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
Navarre Beach
Perdido Key
Warrington

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