HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$139+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SWF
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pensacola to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/45:33 pm
PNS
-
SWF
1 stop16h 35m
Multiple Airlines
Sun 2/811:48 am
SWF
-
PNS
1 stop29h 49m
Multiple Airlines
Deal found 1/20$296
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 6/171:47 pm
PNS
-
SWF
1 stop18h 51m
Multiple Airlines
Tue 6/2311:48 am
SWF
-
PNS
1 stop10h 46m
Multiple Airlines
Deal found 1/19$321
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 5/217:38 pm
PNS
-
SWF
1 stop12h 13m
Multiple Airlines
Mon 5/259:41 am
SWF
-
PNS
1 stop12h 40m
Multiple Airlines
Deal found 1/21$431
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/137:31 pm
PNS
-
SWF
1 stop22h 08m
Multiple Airlines
Sun 2/157:28 pm
SWF
-
PNS
1 stop20h 04m
Multiple Airlines
Deal found 1/20$514
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:38 pm
PNS
-
SWF
2 stops14h 57m
Breeze Airways
Sat 5/912:05 pm
SWF
-
PNS
2 stops21h 06m
Breeze Airways
Deal found 1/20$626

Find 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$296
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$315
Provider with most accurate pricing for Pensacola-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pensacola-New Windsor Stewart flights.
Search Deals
From Pensacola to New Windsor Stewart
Search Deals
One-way flight from Pensacola to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 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 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 January 21, 2026.
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

Wed 2/4

5:33 pm-11:08 am

1 stop16h 35m

New Windsor Stewart

Sun 2/8

11:48 am-4:37 pm

1 stop29h 49m

$296

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Fri 2/13

7:31 pm-6:39 pm

1 stop22h 08m

New Windsor Stewart

Sun 2/15

7:28 pm-2:32 pm

1 stop20h 04m

$514

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 4/19

6:00 am-10:55 am

1 stop27h 55m

$139

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Thu 2/5

4:03 pm-10:19 am

1 stop17h 16m

$147

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 3/1

6:37 pm-10:13 am

1 stop14h 36m

$152

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 2/1

8:15 am-10:19 am

2 stops25h 04m

$178

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 4/12

7:00 am-10:50 am

1 stop26h 50m

$179

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sat 1/31

5:33 pm-11:33 am

1 stop17h 00m

$199

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Thu 2/19

6:37 pm-10:14 am

1 stop14h 37m

$216

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 1/25

5:33 pm-6:43 pm

1 stop24h 10m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Compare providers for flights from Pensacola to Stewart

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

*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 Pensacola-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pensacola-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pensacola-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pensacola-New Windsor flights, Cheapflights users trust Expedia the most. Expedia 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 Pensacola-New Windsor 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 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, April is the cheapest month in which you can book a flight from Pensacola to New Windsor (average of $105). Flying from Pensacola to New Windsor in December is currently the most expensive (average of $183). 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.

  • 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, April is the cheapest month in which you can book a flight from Pensacola to New Windsor (average of $105). Flying from Pensacola to New Windsor in December is currently the most expensive (average of $183). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Pensacola to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Miami to John F Kennedy Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Miami to LaGuardia flights
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Miami to Newark flights
Tampa to John F Kennedy Intl flights
Tampa to Newark flights
West Palm Beach to Newark flights
Tampa to LaGuardia flights
Orlando to Newark flights
Orlando to LaGuardia flights
West Palm Beach to John F Kennedy Intl flights
West Palm Beach to LaGuardia flights
Jacksonville to John F Kennedy Intl flights
Jacksonville to Newark flights
Jacksonville to LaGuardia flights
Fort Myers to John F Kennedy Intl flights
Fort Myers to Newark flights
Orlando to White Plains flights
Sarasota to John F Kennedy Intl flights
Fort Myers to LaGuardia flights
Sarasota to Newark flights
Orlando to Stewart flights
Sarasota to LaGuardia flights
Pensacola to LaGuardia flights
Orlando to Buffalo flights
Tampa to Islip flights
Fort Lauderdale to White Plains flights
Orlando to Islip flights
West Palm Beach to Islip flights
Pensacola to John F Kennedy Intl flights
Tampa to White Plains flights
Orlando to Syracuse flights
Gainesville to John F Kennedy Intl flights
Pensacola to Newark flights
Gainesville to LaGuardia flights
Orlando to Albany flights
Daytona Beach to John F Kennedy Intl flights
Fort Lauderdale to Stewart flights
Fort Myers to White Plains flights
West Palm Beach to White Plains flights
Orlando to Rochester flights
Fort Lauderdale to Buffalo flights
Panama City to LaGuardia flights
Tallahassee to John F Kennedy Intl flights
Tampa to Albany flights
Fort Lauderdale to Albany flights
Fort Lauderdale to Islip flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.