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Cheap flights from Winnipeg to Wisconsin from C$ 174

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 30/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MKE
5 ago. — 12 ago.1
1 adult

Cheap flight deals from Winnipeg to Wisconsin

Keep the following information in mind while searching for Winnipeg to Wisconsin flight deals. Data was last updated 31 julio 2025.

Round-trip from

C$ 293

One-way from

C$ 174
WestJet
  • WestJet
  • 24/9-27/9
  • 2 total stops
  • 15h 58m total
  • Winnipeg to Wisconsin
Search Deals
WestJet
  • WestJet
  • 30/9
  • 1 total stop
  • 23h 38m total
  • Winnipeg to Wisconsin
Search Deals

Find flight deals from Winnipeg to Wisconsin

Cheapest flights from Winnipeg to Wisconsin
Explore the most affordable flight options available from Winnipeg to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 julio 2025.

mié. 24/98:30 a.m.YWG - ORD
1 stop8h 13mWestJet
sáb. 27/91:40 p.m.ORD - YWG
1 stop7h 45mWestJet
Deal found 30/7C$ 293
dom. 24/86:30 a.m.YWG - MSP
1 stop6h 42mWestJet
dom. 31/82:00 p.m.MSP - YWG
1 stop7h 26mWestJet
Deal found 31/7C$ 303
sáb. 13/97:00 p.m.YWG - ORD
2 stops14h 51mMultiple Airlines
sáb. 20/91:40 p.m.ORD - YWG
1 stop7h 45mMultiple Airlines
Deal found 30/7C$ 405
vie. 12/912:00 p.m.YWG - ORD
1 stop8h 11mAir Canada
vie. 19/910:40 a.m.ORD - YWG
1 stop8h 19mAir Canada
Deal found 29/7C$ 448
jue. 18/92:20 p.m.YWG - ORD
Nonstop2h 31mUnited Airlines
dom. 21/91:01 p.m.ORD - YWG
Nonstop2h 30mUnited Airlines
Deal found 31/7C$ 465

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Wisconsin 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 31 julio 2025.
Use the filters below to find and compare flights from Winnipeg to Wisconsin that are best for you.

Fly from

Winnipeg

Fly to

Wisconsin

Route

Depart

Return

Price

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mié. 24/9

8:30 a.m.-4:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

sáb. 27/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 293

WinnipegMinneapolis

YWG - MSP

YWGMSP

Winnipeg

dom. 24/8

6:30 a.m.-1:12 p.m.

1 stop6h 42m

Minneapolis St Paul

dom. 31/8

2:00 p.m.-9:26 p.m.

1 stop7h 26m

C$ 303

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 13/9

7:00 p.m.-9:51 a.m.

2 stops14h 51m

Chicago O'Hare Intl

sáb. 20/9

1:40 p.m.-9:25 p.m.

1 stop7h 45m

C$ 405

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 12/9

12:00 p.m.-8:11 p.m.

1 stop8h 11m

Chicago O'Hare Intl

vie. 19/9

10:40 a.m.-6:59 p.m.

1 stop8h 19m

C$ 448

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jue. 18/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

Chicago O'Hare Intl

dom. 21/9

1:01 p.m.-3:31 p.m.

Nonstop2h 30m

C$ 465

WinnipegMinneapolis

YWG - MSP

YWGMSP

Winnipeg

mar. 30/9

6:55 p.m.-6:33 p.m.

1 stop23h 38m

C$ 174

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mar. 9/9

5:30 p.m.-4:43 p.m.

1 stop23h 13m

C$ 206

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

mar. 2/9

8:55 p.m.-4:43 p.m.

1 stop19h 48m

C$ 224

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 5/9

2:20 p.m.-4:51 p.m.

Nonstop2h 31m

C$ 266

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 20/9

12:00 p.m.-8:11 p.m.

1 stop8h 11m

C$ 274

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/7

Showing 1-10 of 13 results
1
2

Best time to book a flight from Winnipeg to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin 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.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Wisconsin

What is the cheapest time of day to fly from YWG to WI?

Find hourly flight availability from Winnipeg to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 31 julio 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Wisconsin as you normally would.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated 31 julio 2025.
Get a feel of what it's like to fly with United Airlines,WestJet, andAir Canada from Winnipeg to Wisconsin by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,900 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,900 reviews
United Airlines
7.4
Good
8,900 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
WestJet
7.2
Good
2,978 reviews
United Airlines
7.4
Good
8,900 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
9,851 reviews
United Airlines
7.4
Good
8,900 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

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

  • What airport do you fly from for flights from Winnipeg to Wisconsin?

    Winnipeg (YWG) is the airport you will fly out of if you book a flight from Winnipeg to Wisconsin. It is only a 7.3 km journey to Winnipeg (YWG) from Winnipeg’s city centre.

  • What are the cheapest airlines to fly from Winnipeg to Wisconsin one-way?

    The cheapest airlines for a one-way flight from Winnipeg to Wisconsin are WestJet (C$ 174), United Airlines (C$ 266), and Air Canada (C$ 274).

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Winnipeg to Wisconsin (average of C$ 341). Flying from Winnipeg to Wisconsin in July is currently the most expensive (average of C$ 484). 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

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

Yes, Cheapflights offers price alerts on Winnipeg to Wisconsin flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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