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Cheap flights from Winnipeg to Pensacola from C$ 286

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 28/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PNS
15 Feb — 22 Feb1
1 adult
1 adult, Economy, 0 bags

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 16 January 2026.

Round-trip from

C$ 606

One-way from

C$ 286
27/2-1/3
  • 27/2-1/3
  • 6 total stops
  • 64h 16m total
  • Winnipeg to Pensacola
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28/2
  • 28/2
  • 2 total stops
  • 27h 34m total
  • Winnipeg to Pensacola
Search Deals

Find flight deals from Winnipeg to Pensacola

Enter your travel dates to find the best prices.

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 16 January 2026.

Fri 27/27:30 a.m.
YWG
-
PNS
3 stops34h 12m
Multiple Airlines
Sun 1/36:37 p.m.
PNS
-
YWG
3 stops30h 04m
Multiple Airlines
Deal found 14/1C$ 606
Mon 2/32:20 p.m.
YWG
-
PNS
2 stops19h 20m
United Airlines
Mon 9/36:30 a.m.
PNS
-
YWG
2 stops29h 27m
United Airlines
Deal found 15/1C$ 800
Fri 27/212:10 p.m.
YWG
-
PNS
2 stops22h 11m
American Airlines
Sun 1/35:23 a.m.
PNS
-
YWG
2 stops18h 12m
American Airlines
Deal found 14/1C$ 838
Fri 27/27:30 a.m.
YWG
-
PNS
1 stop13h 20m
Delta
Sun 1/36:00 a.m.
PNS
-
YWG
1 stop9h 09m
Delta
Deal found 14/1C$ 884
Fri 27/212:20 p.m.
YWG
-
PNS
2 stops10h 51m
WestJet
Sun 1/39:03 a.m.
PNS
-
YWG
1 stop6h 06m
WestJet
Deal found 14/1C$ 949
Sun 18/12:20 p.m.
YWG
-
PNS
2 stops19h 20m
United Airlines
Thu 22/110:30 a.m.
PNS
-
YWG
2 stops25h 27m
United Airlines
Deal found 15/1C$ 1,272

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 629,999 searches. Data last updated 16 January 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

Fri 27/2

7:30 a.m.-5:42 p.m.

3 stops34h 12m

Pensacola

Sun 1/3

6:37 p.m.-12:41 a.m.

3 stops30h 04m

C$ 606

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Mon 2/3

2:20 p.m.-9:40 a.m.

2 stops19h 20m

Pensacola

Mon 9/3

6:30 a.m.-11:57 a.m.

2 stops29h 27m

C$ 800

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 27/2

12:10 p.m.-10:21 a.m.

2 stops22h 11m

Pensacola

Sun 1/3

5:23 a.m.-11:35 p.m.

2 stops18h 12m

C$ 838

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 27/2

7:30 a.m.-8:50 p.m.

1 stop13h 20m

Pensacola

Sun 1/3

6:00 a.m.-3:09 p.m.

1 stop9h 09m

C$ 884

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 27/2

12:20 p.m.-11:11 p.m.

2 stops10h 51m

Pensacola

Sun 1/3

9:03 a.m.-3:09 p.m.

1 stop6h 06m

C$ 949

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sat 28/2

12:20 p.m.-3:54 p.m.

2 stops27h 34m

C$ 286

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sun 1/3

7:30 a.m.-8:18 a.m.

1 stop24h 48m

C$ 585

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Sun 1/3

7:20 p.m.-6:08 p.m.

3 stops22h 48m

C$ 677

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/1

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?

    A quick flight from Winnipeg to Pensacola can take about 13h 20m. United Airlines provides one of the quickest options available for as low as C$ 884. The distance from Winnipeg to Pensacola is about 2316 km. This flight may include one or multiple 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.

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When you search for this flight from Winnipeg to Pensacola, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Pensacola?

Millions of users choose and trust Cheapflights to book the best flight deals from Winnipeg to Pensacola for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Winnipeg to Pensacola with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Pensacola, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Winnipeg to Pensacola become cheaper?

Of course! You can now track prices for flights from Winnipeg to Pensacola and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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