HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pensacola

$188+ Cheap flights from Winnipeg (YWG) to Pensacola (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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PNS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Pensacola 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 Winnipeg to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) 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 September 17, 2025.

Round-trip from

$554
(United Airlines)

One-way from

$188
(Kiwi.com)
From Winnipeg to Pensacola
Search Deals
One-way flight from Winnipeg to Pensacola
Search Deals

Find flight deals from Winnipeg to Pensacola

Cheapest flights from Winnipeg to Pensacola
Explore the most affordable flight options available from Winnipeg to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/16. 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.
Sun 10/59:05 pmYWG - PNS
3 stops18h 26mMultiple Airlines
Wed 10/155:56 pmPNS - YWG
3 stops29h 14mMultiple Airlines
Deal found 9/16$577
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:35 pmYWG - PNS
2 stops21h 44mUnited Airlines
Wed 10/223:00 pmPNS - YWG
2 stops22h 09mUnited Airlines
Deal found 9/17$583
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:30 amYWG - PNS
2 stops12h 24mWestJet
Wed 10/151:42 pmPNS - YWG
2 stops10h 48mWestJet
Deal found 9/16$619
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/57:00 amYWG - PNS
1 stop6h 15mUnited Airlines
Wed 10/152:17 pmPNS - YWG
1 stop8h 16mUnited Airlines
Deal found 9/16$752

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg 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 September 17, 2025.
Use the filters below to find and compare flights from Winnipeg to Pensacola that are best for you.

Fly from

Winnipeg

Fly to

Pensacola

Route

Depart

Return

Price

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Tue 3/10

2:15 pm-11:10 am

2 stops20h 55m

Pensacola

Wed 3/11

4:52 pm-11:39 am

2 stops18h 47m

$554

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sun 10/5

9:05 pm-3:31 pm

3 stops18h 26m

Pensacola

Wed 10/15

5:56 pm-11:10 pm

3 stops29h 14m

$577

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Wed 10/15

6:35 pm-4:19 pm

2 stops21h 44m

Pensacola

Wed 10/22

3:00 pm-1:09 pm

2 stops22h 09m

$583

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Wed 10/15

11:20 am-3:31 pm

3 stops28h 11m

Pensacola

Wed 10/22

5:56 pm-11:10 pm

3 stops29h 14m

$594

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sun 10/5

6:30 am-6:54 pm

2 stops12h 24m

Pensacola

Wed 10/15

1:42 pm-12:30 am

2 stops10h 48m

$619

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Tue 3/10

6:15 am-4:34 pm

2 stops10h 19m

Pensacola

Wed 3/11

6:00 am-3:09 pm

1 stop9h 09m

$682

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 10/31

7:30 am-4:04 pm

2 stops32h 34m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Best time to book a flight from Winnipeg to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from Winnipeg 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.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Pensacola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Winnipeg to Pensacola?

    For as low as $554, United Airlines can have you in Pensacola from Winnipeg in 20h 55m. The distance between Winnipeg and Pensacola is about 1439 mi.

  • Can I find deals for flights from Winnipeg to Pensacola that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Pensacola.

  • Can I find deals for business class flights from Winnipeg to Pensacola?

    Yes. Cheapflights offers flight deals from Winnipeg 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 Winnipeg to Pensacola?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Pensacola (average of $302). Flying from Winnipeg to Pensacola in March is currently the most expensive (average of $415). 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

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.

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.