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Cheap flights from Winnipeg to Pensacola from C$ 536

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 17/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PNS
15 Oct — 22 Oct1
1 adult
1 adult, Economy

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 15 September 2025.

Round-trip from

C$ 729
United Airlines
  • United Airlines
  • 20/2-27/2
  • 4 total stops
  • 55h 54m total
  • Winnipeg to Pensacola
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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 15 September 2025.

Fri 17/109:00 a.m.YWG - PNS
2 stops31h 04mMultiple Airlines
Fri 24/106:25 p.m.PNS - YWG
1 stop24h 07mMultiple Airlines
Deal found 13/9C$ 536
Thu 16/109:00 a.m.YWG - PNS
2 stops30h 31mMultiple Airlines
Fri 24/106:25 p.m.PNS - YWG
1 stop24h 07mMultiple Airlines
Deal found 13/9C$ 539
Wed 15/1011:20 a.m.YWG - PNS
2 stops21h 54mMultiple Airlines
Fri 24/106:25 p.m.PNS - YWG
1 stop24h 07mMultiple Airlines
Deal found 13/9C$ 608
Sun 12/108:10 p.m.YWG - PNS
2 stops19h 21mMultiple Airlines
Fri 24/106:25 p.m.PNS - YWG
1 stop24h 07mMultiple Airlines
Deal found 13/9C$ 656
Tue 14/107:00 p.m.YWG - PNS
2 stops22h 01mMultiple Airlines
Fri 24/106:25 p.m.PNS - YWG
1 stop24h 07mMultiple Airlines
Deal found 13/9C$ 664
Sat 11/1011:20 a.m.YWG - PNS
2 stops52h 11mMultiple Airlines
Fri 24/106:25 p.m.PNS - YWG
1 stop24h 07mMultiple Airlines
Deal found 13/9C$ 706
Mon 13/106:30 a.m.YWG - PNS
2 stops14h 47mMultiple Airlines
Fri 24/106:25 p.m.PNS - YWG
1 stop24h 07mMultiple Airlines
Deal found 13/9C$ 760
Tue 14/107:00 a.m.YWG - PNS
1 stop6h 15mUnited Airlines
Wed 22/107:00 a.m.PNS - YWG
2 stops30h 09mUnited Airlines
Deal found 13/9C$ 781
Wed 15/106:30 a.m.YWG - PNS
2 stops8h 35mWestJet
Thu 23/1011:45 a.m.PNS - YWG
2 stops12h 45mWestJet
Deal found 13/9C$ 823
Sat 11/109:10 a.m.YWG - PNS
1 stop24h 04mMultiple Airlines
Wed 22/105:56 p.m.PNS - YWG
2 stops22h 26mMultiple Airlines
Deal found 13/9C$ 845
Mon 13/106:30 a.m.YWG - PNS
2 stops10h 28mWestJet
Wed 22/101:42 p.m.PNS - YWG
2 stops10h 48mWestJet
Deal found 13/9C$ 850

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 15 September 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

Fri 20/2

11:05 a.m.-4:02 p.m.

2 stops28h 57m

Pensacola

Fri 27/2

9:00 a.m.-11:57 a.m.

2 stops26h 57m

C$ 729

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 20/2

7:30 a.m.-6:03 p.m.

1 stop10h 33m

Pensacola

Fri 27/2

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

1 stop9h 09m

C$ 734

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 20/2

7:30 a.m.-6:03 p.m.

1 stop10h 33m

Pensacola

Thu 26/2

5:45 p.m.-3:09 p.m.

1 stop21h 24m

C$ 734

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Fri 20/2

7:30 a.m.-6:03 p.m.

1 stop10h 33m

Pensacola

Sat 28/2

5:00 p.m.-3:09 p.m.

1 stop22h 09m

C$ 734

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Tue 10/3

2:15 p.m.-11:10 a.m.

2 stops20h 55m

Pensacola

Wed 11/3

4:52 p.m.-11:39 a.m.

2 stops18h 47m

C$ 765

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 19/2

5:38 p.m.-8:47 a.m.

2 stops15h 09m

Pensacola

Fri 27/2

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

1 stop9h 09m

C$ 794

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 19/2

5:38 p.m.-8:47 a.m.

2 stops15h 09m

Pensacola

Sat 28/2

5:00 p.m.-3:09 p.m.

1 stop22h 09m

C$ 794

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 19/2

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

2 stops19h 20m

Pensacola

Fri 27/2

5:08 p.m.-11:57 a.m.

2 stops18h 49m

C$ 833

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 19/2

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

2 stops19h 20m

Pensacola

Sat 28/2

5:08 p.m.-11:57 a.m.

2 stops18h 49m

C$ 833

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

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.

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pensacola. Reviews last updated 15 September 2025.
See what other customers who have flown with WestJet from Winnipeg to Pensacola have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,091 reviews
Check prices

Overall

7.2

Food

6.2

Comfort

7.1

Boarding

7.4

Entertainment

6.1

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,091 reviews
WestJet
7.2
Good
3,091 reviews
Check prices

Overall

7.2

Food

6.2

Comfort

7.1

Boarding

7.4

Entertainment

6.1

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

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 10h 33m. United Airlines provides one of the quickest options available for as low as C$ 734. The distance from Winnipeg to Pensacola is about 2316 km. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Winnipeg to Pensacola round-trip?

    Flying on WestJet is currently your cheapest option to Pensacola, with prices starting at C$ 890.

  • 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, November is the cheapest month in which you can book a flight from Winnipeg to Pensacola (average of C$ 262). Flying from Winnipeg to Pensacola in May is currently the most expensive (average of C$ 403). 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Winnipeg to Pensacola

Discover the top airline that operate flights from Winnipeg to Pensacola. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 15 September 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 890AverageC$ 1,038FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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How does Cheapflights help users find flights from Winnipeg to Pensacola?

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.

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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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