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Pensacola

$112+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — PNS
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/1212:27 pmSWF - PNS
1 stop6h 47mMultiple Airlines
Thu 12/187:09 pmPNS - SWF
1 stop21h 57mMultiple Airlines
Deal found 12/8$423
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.
Mon 12/228:25 pmSWF - PNS
1 stop17h 38mMultiple Airlines
Mon 12/293:35 pmPNS - SWF
2 stops18h 28mMultiple Airlines
Deal found 12/9$653
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:40 amSWF - PNS
3 stops32h 34mMultiple Airlines
Sun 12/287:09 pmPNS - SWF
1 stop14h 38mMultiple Airlines
Deal found 12/9$655
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.
Tue 12/2311:43 amSWF - PNS
2 stops29h 21mMultiple Airlines
Sun 12/287:09 pmPNS - SWF
1 stop14h 38mMultiple Airlines
Deal found 12/9$768
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:40 amSWF - PNS
3 stops32h 34mMultiple Airlines
Tue 12/301:58 pmPNS - SWF
3 stops25h 46mMultiple Airlines
Deal found 12/9$795
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2911:37 amSWF - PNS
1 stop7h 37mMultiple Airlines
Thu 1/17:09 pmPNS - SWF
1 stop14h 58mMultiple Airlines
Deal found 12/11$799
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/209:45 amSWF - PNS
3 stops33h 29mMultiple Airlines
Tue 12/231:58 pmPNS - SWF
3 stops25h 46mMultiple Airlines
Deal found 12/9$875

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$314
(Kiwi.com)

One-way from

$112
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$602
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. 7% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 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 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 December 12, 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 2/12

11:42 am-3:56 pm

1 stop29h 14m

Pensacola

Wed 2/18

4:51 pm-11:32 am

1 stop17h 41m

$314

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/22

8:25 pm-1:03 pm

1 stop17h 38m

Pensacola

Mon 12/29

3:35 pm-11:03 am

2 stops18h 28m

$653

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Wed 12/24

10:40 am-6:14 pm

3 stops32h 34m

Pensacola

Sun 12/28

7:09 pm-10:47 am

1 stop14h 38m

$655

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Tue 12/23

11:43 am-4:04 pm

2 stops29h 21m

Pensacola

Sun 12/28

7:09 pm-10:47 am

1 stop14h 38m

$768

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Wed 12/24

10:40 am-6:14 pm

3 stops32h 34m

Pensacola

Tue 12/30

1:58 pm-4:44 pm

3 stops25h 46m

$795

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/29

11:37 am-6:14 pm

1 stop7h 37m

Pensacola

Thu 1/1

7:09 pm-11:07 am

1 stop14h 58m

$799

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 1/5

11:37 am-1:03 pm

1 stop26h 26m

$112

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Fri 12/19

12:24 pm-6:14 pm

2 stops30h 50m

$284

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/22

8:25 pm-4:04 pm

2 stops44h 39m

$328

New WindsorPensacola

SWF - PNS

SWFPNS

New Windsor Stewart

Mon 12/22

12:24 pm-7:31 am

2 stops20h 07m

$491

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

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 December.
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 May is currently the most expensive (average of $197). 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 May is currently the most expensive (average of $197). 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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