HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$129+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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

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 September 11, 2025.

Round-trip from

$238
(Kiwi.com)

One-way from

$129
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$298
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. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find 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 September 11, 2025.

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.
Thu 11/134:41 pmPNS - SWF
1 stop16h 30mMultiple Airlines
Mon 11/1712:01 pmSWF - PNS
1 stop28h 35mMultiple Airlines
Deal found 9/10$238
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.
Sun 11/94:41 pmPNS - SWF
1 stop17h 30mMultiple Airlines
Mon 11/1712:01 pmSWF - PNS
1 stop28h 35mMultiple Airlines
Deal found 9/10$269
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.
Sun 11/94:41 pmPNS - SWF
1 stop17h 30mMultiple Airlines
Fri 11/1411:01 amSWF - PNS
1 stop22h 56mMultiple Airlines
Deal found 9/10$271
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 10/94:36 pmPNS - SWF
1 stop17h 15mMultiple Airlines
Sun 10/1211:43 amSWF - PNS
1 stop7h 32mMultiple Airlines
Deal found 9/9$305
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 11/74:41 pmPNS - SWF
2 stops43h 01mMultiple Airlines
Mon 11/1712:01 pmSWF - PNS
1 stop28h 35mMultiple Airlines
Deal found 9/10$339
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 11/74:41 pmPNS - SWF
2 stops43h 01mMultiple Airlines
Fri 11/1411:01 amSWF - PNS
1 stop22h 56mMultiple Airlines
Deal found 9/10$341
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.
Thu 11/134:41 pmPNS - SWF
1 stop16h 30mMultiple Airlines
Sun 11/161:32 pmSWF - PNS
2 stops29h 22mMultiple Airlines
Deal found 9/10$347
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.
Sun 11/94:41 pmPNS - SWF
1 stop17h 30mMultiple Airlines
Sun 11/161:32 pmSWF - PNS
2 stops29h 22mMultiple Airlines
Deal found 9/10$379
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.
Sun 11/94:41 pmPNS - SWF
1 stop17h 30mMultiple Airlines
Thu 11/131:32 pmSWF - PNS
2 stops29h 22mMultiple Airlines
Deal found 9/10$380

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 September 11, 2025.
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

Thu 11/13

4:41 pm-10:11 am

1 stop16h 30m

New Windsor Stewart

Mon 11/17

12:01 pm-3:36 pm

1 stop28h 35m

$238

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 11/9

4:41 pm-11:11 am

1 stop17h 30m

New Windsor Stewart

Mon 11/17

12:01 pm-3:36 pm

1 stop28h 35m

$269

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 11/9

4:41 pm-11:11 am

1 stop17h 30m

New Windsor Stewart

Fri 11/14

11:01 am-8:57 am

1 stop22h 56m

$271

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Thu 10/9

4:36 pm-10:51 am

1 stop17h 15m

New Windsor Stewart

Sun 10/12

11:43 am-6:15 pm

1 stop7h 32m

$305

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Fri 11/7

4:41 pm-12:42 pm

2 stops43h 01m

New Windsor Stewart

Mon 11/17

12:01 pm-3:36 pm

1 stop28h 35m

$339

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Fri 11/7

4:41 pm-12:42 pm

2 stops43h 01m

New Windsor Stewart

Fri 11/14

11:01 am-8:57 am

1 stop22h 56m

$341

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Thu 11/13

4:41 pm-10:11 am

1 stop16h 30m

New Windsor Stewart

Sun 11/16

1:32 pm-5:54 pm

2 stops29h 22m

$347

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 11/9

4:41 pm-11:11 am

1 stop17h 30m

New Windsor Stewart

Sun 11/16

1:32 pm-5:54 pm

2 stops29h 22m

$379

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Sun 11/9

4:41 pm-11:11 am

1 stop17h 30m

New Windsor Stewart

Thu 11/13

1:32 pm-5:54 pm

2 stops29h 22m

$380

PensacolaNew Windsor

PNS - SWF

PNSSWF

Pensacola

Tue 11/25

4:41 pm-11:27 am

1 stop17h 46m

New Windsor Stewart

Mon 12/1

5:49 pm-5:54 pm

2 stops49h 05m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 18 results
1
2

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, October is the cheapest month in which you can book a flight from Pensacola to New Windsor (average of $109). Flying from Pensacola to New Windsor in December is currently the most expensive (average of $202). 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, October is the cheapest month in which you can book a flight from Pensacola to New Windsor (average of $109). Flying from Pensacola to New Windsor in December is currently the most expensive (average of $202). 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.
Fort Lauderdale to LaGuardia flights
Miami to John F Kennedy Intl flights
Fort Lauderdale to Newark flights
Miami to LaGuardia flights
Miami to Newark flights
Orlando to John F Kennedy Intl flights
Tampa to LaGuardia flights
Fort Lauderdale to John F Kennedy Intl flights
Tampa to John F Kennedy Intl flights
Orlando to LaGuardia flights
Tampa to Newark flights
Orlando to Newark flights
West Palm Beach to John F Kennedy Intl flights
West Palm Beach to Newark flights
Jacksonville to John F Kennedy Intl flights
Jacksonville to LaGuardia flights
West Palm Beach to LaGuardia flights
Jacksonville to Newark flights
Orlando to Islip flights
Fort Myers to John F Kennedy Intl flights
Fort Myers to Newark flights
Tampa to Islip flights
Fort Lauderdale to Buffalo flights
Orlando to Buffalo flights
Sarasota to John F Kennedy Intl flights
Tampa to Buffalo flights
Sarasota to Newark flights
Fort Myers to LaGuardia flights
Orlando to White Plains flights
Orlando to Stewart flights
Sarasota to LaGuardia flights
Tampa to White Plains flights
Orlando to Syracuse flights
Pensacola to LaGuardia flights
Fort Lauderdale to Stewart flights
West Palm Beach to Islip flights
West Palm Beach to White Plains flights
Miami to Buffalo flights
Fort Lauderdale to White Plains flights
Tampa to Stewart flights
Orlando to Albany flights
Fort Lauderdale to Islip flights
Pensacola to John F Kennedy Intl flights
Pensacola to Newark flights
Gainesville to John F Kennedy Intl flights
West Palm Beach to Buffalo flights
Orlando to Rochester flights
Tampa to Albany flights
Gainesville to Newark flights
Fort Myers to White Plains 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.