HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pensacola

$317+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PNS
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
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

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 February 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/15. 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 3/196:00 am
YWG
-
PNS
2 stops39h 14m
Multiple Airlines
Fri 3/277:00 am
PNS
-
YWG
1 stop18h 26m
Multiple Airlines
Deal found 2/15$394
This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:40 pm
YWG
-
PNS
2 stops20h 02m
Delta
Sat 7/118:00 am
PNS
-
YWG
2 stops15h 27m
Delta
Deal found 2/16$544
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Sat 7/47:00 am
YWG
-
PNS
1 stop6h 20m
United Airlines
Sat 7/112:22 pm
PNS
-
YWG
1 stop8h 02m
United Airlines
Deal found 2/16$578
This United Airlines deal was found by Cheapflights users on 2/15. 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.
Mon 3/22:20 pm
YWG
-
PNS
2 stops19h 20m
United Airlines
Wed 3/45:08 pm
PNS
-
YWG
2 stops18h 49m
United Airlines
Deal found 2/15$602
This United Airlines deal was found by Cheapflights users on 2/17. 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.
Fri 5/88:45 am
YWG
-
PNS
2 stops25h 04m
United Airlines
Sun 5/106:30 am
PNS
-
YWG
2 stops14h 27m
United Airlines
Deal found 2/17$609
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2811:53 am
YWG
-
PNS
2 stops20h 25m
Delta
Sat 3/75:00 pm
PNS
-
YWG
2 stops22h 23m
Delta
Deal found 2/15$610
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1912:10 pm
YWG
-
PNS
2 stops22h 11m
American Airlines
Fri 3/277:26 am
PNS
-
YWG
2 stops16h 09m
American Airlines
Deal found 2/15$624
This Mytrip deal was found by Cheapflights users on 2/15. 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.
Fri 2/278:20 pm
YWG
-
PNS
2 stops21h 22m
Multiple Airlines
Fri 3/66:37 pm
PNS
-
YWG
3 stops25h 08m
Multiple Airlines
Deal found 2/15$674
This American Airlines deal was found by Cheapflights users on 2/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2712:10 pm
YWG
-
PNS
2 stops27h 41m
American Airlines
Fri 3/67:26 am
PNS
-
YWG
2 stops16h 09m
American Airlines
Deal found 2/15$706

Find 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 February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$394
(Kiwi.com)

One-way from

$317
(United Airlines)
Provider with most accurate pricing for Winnipeg-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Pensacola flights.
Search Deals
From Winnipeg to Pensacola
Search Deals
One-way flight from Winnipeg to Pensacola
Search Deals

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 February 18, 2026.
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

Thu 3/19

6:00 am-9:14 pm

2 stops39h 14m

Pensacola

Fri 3/27

7:00 am-1:26 am

1 stop18h 26m

$394

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sat 7/4

12:40 pm-8:42 am

2 stops20h 02m

Pensacola

Sat 7/11

8:00 am-11:27 pm

2 stops15h 27m

$544

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sat 7/4

7:00 am-1:20 pm

1 stop6h 20m

Pensacola

Sat 7/11

2:22 pm-10:24 pm

1 stop8h 02m

$578

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 5/8

8:45 am-9:59 pm

2 stops13h 14m

Pensacola

Sun 5/10

6:30 am-8:57 pm

2 stops14h 27m

$578

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Mon 3/2

2:20 pm-9:40 am

2 stops19h 20m

Pensacola

Wed 3/4

9:00 am-11:57 am

2 stops26h 57m

$602

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sat 2/28

11:53 am-8:18 am

2 stops20h 25m

Pensacola

Sat 3/7

5:00 pm-3:23 pm

2 stops22h 23m

$610

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 3/19

12:10 pm-10:21 am

2 stops22h 11m

Pensacola

Fri 3/27

7:26 am-11:35 pm

2 stops16h 09m

$624

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 4/3

8:45 am-8:00 pm

2 stops11h 15m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

  • Most accurate provider: When it comes to deals on Winnipeg-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-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 Winnipeg-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 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 $578, Delta can have you in Pensacola from Winnipeg in 6h 20m. The distance between Winnipeg and Pensacola is about 1439 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

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

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.
Site
©2026 Cheapflights