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Pensacola

$360+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PNS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. 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 2/72:20 pm
YWG
-
PNS
2 stops19h 20m
United Airlines
Tue 2/109:00 am
PNS
-
YWG
2 stops26h 57m
United Airlines
Deal found 1/28$835
This WestJet deal was found by Cheapflights users on 1/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:15 pm
YWG
-
PNS
2 stops30h 47m
WestJet
Mon 5/185:45 pm
PNS
-
YWG
2 stops23h 40m
WestJet
Deal found 1/27$908
This United Airlines deal was found by Cheapflights users on 1/26. 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 1/312:20 pm
YWG
-
PNS
2 stops19h 20m
United Airlines
Wed 2/410:40 am
PNS
-
YWG
2 stops25h 17m
United Airlines
Deal found 1/26$921
This WestJet deal was found by Cheapflights users on 1/26. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/319:00 pm
YWG
-
PNS
2 stops15h 35m
WestJet
Wed 2/49:23 am
PNS
-
YWG
1 stop5h 46m
WestJet
Deal found 1/26$1,097
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/287:05 pm
YWG
-
PNS
2 stops23h 11m
Air Canada
Thu 2/59:00 am
PNS
-
YWG
2 stops12h 44m
Air Canada
Deal found 1/28$1,190
This Air Canada deal was found by Cheapflights users on 1/27. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:00 pm
YWG
-
PNS
1 stop23h 09m
Multiple Airlines
Mon 5/182:11 pm
PNS
-
YWG
1 stop21h 41m
Multiple Airlines
Deal found 1/27$1,600
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/287:05 pm
YWG
-
PNS
2 stops23h 11m
Multiple Airlines
Thu 2/52:13 pm
PNS
-
YWG
1 stop21h 44m
Multiple Airlines
Deal found 1/28$1,684

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$908
(WestJet)

One-way from

$360
(Delta)
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
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One-way flight from Winnipeg to Pensacola
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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 January 29, 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 5/14

3:15 pm-10:02 pm

2 stops30h 47m

Pensacola

Mon 5/18

5:45 pm-5:25 pm

2 stops23h 40m

$908

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 5/14

2:00 pm-1:09 pm

1 stop23h 09m

Pensacola

Mon 5/18

2:11 pm-11:52 am

1 stop21h 41m

$1,600

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 5/14

6:40 am-10:02 pm

2 stops15h 22m

$360

WinnipegPensacola

YWG - PNS

YWGPNS

Winnipeg

Thu 5/14

2:00 pm-1:09 pm

1 stop23h 09m

$540

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

  • 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 $908, WestJet can have you in Pensacola from Winnipeg in 30h 47m. 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.

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

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