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Cheap flights from Wisconsin to Winnipeg from C$ 182

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
23 Apr — 30 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Wisconsin to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Wisconsin to Winnipeg
Explore the most affordable flight options available from Wisconsin to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 24 March 2026.

Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 3/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 20/3C$ 440
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 4/59:05 p.m.
YWG
-
ORD
2 stops22h 46m
Multiple Airlines
Deal found 20/3C$ 465
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 3/59:05 p.m.
YWG
-
ORD
2 stops25h 34m
Multiple Airlines
Deal found 20/3C$ 469
Sun 3/55:30 p.m.
ORD
-
YWG
1 stop18h 45m
WestJet
Sun 10/57:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 19/3C$ 487
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 2/59:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 20/3C$ 490
Thu 14/55:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 19/59:05 p.m.
YWG
-
ORD
2 stops13h 41m
Multiple Airlines
Deal found 22/3C$ 491
Sun 26/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 2/57:10 p.m.
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 22/3C$ 516
Sun 10/53:05 p.m.
MSP
-
YWG
1 stop7h 05m
WestJet
Sat 16/57:00 a.m.
YWG
-
MSP
1 stop6h 25m
WestJet
Deal found 22/3C$ 517
Fri 22/52:55 p.m.
MSP
-
YWG
1 stop6h 45m
WestJet
Mon 25/57:00 a.m.
YWG
-
MSP
1 stop6h 25m
WestJet
Deal found 19/3C$ 519
Thu 7/52:55 p.m.
MSP
-
YWG
1 stop6h 45m
WestJet
Mon 18/57:00 a.m.
YWG
-
MSP
1 stop6h 25m
WestJet
Deal found 22/3C$ 520
Thu 30/45:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Fri 1/59:20 a.m.
YWG
-
ORD
1 stop6h 58m
Multiple Airlines
Deal found 20/3C$ 523
Fri 1/53:50 p.m.
MSP
-
YWG
2 stops9h 05m
WestJet
Mon 4/57:00 a.m.
YWG
-
MSP
1 stop6h 25m
WestJet
Deal found 22/3C$ 528

Find flight deals from Wisconsin to Winnipeg

Keep the following information in mind while searching for Wisconsin to Winnipeg flight deals. Data was last updated 24 March 2026.

Round-trip from

C$ 440

One-way from

C$ 182
WestJet
  • WestJet
  • 30/4-3/5
  • 2 total stops
  • 17h 05m total
  • Wisconsin to Winnipeg
Search Deals
WestJet
  • WestJet
  • 26/4
  • 1 total stop
  • 7h 25m total
  • Wisconsin to Winnipeg
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Winnipeg 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 24 March 2026.
Use the filters below to find and compare flights from Wisconsin to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Mon 20/7

6:40 p.m.-2:25 p.m.

2 stops19h 45m

Winnipeg

Fri 24/7

3:59 p.m.-7:32 p.m.

1 stop3h 33m

C$ 605

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Mon 17/8

11:53 a.m.-8:09 p.m.

1 stop8h 16m

Winnipeg

Sat 22/8

6:15 a.m.-4:36 p.m.

2 stops10h 21m

C$ 612

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 6/5

6:50 a.m.-2:25 p.m.

2 stops7h 35m

Winnipeg

Wed 13/5

3:50 p.m.-7:47 p.m.

1 stop3h 57m

C$ 628

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 29/5

2:35 p.m.-10:33 p.m.

1 stop7h 58m

Winnipeg

Sat 30/5

7:00 a.m.-2:00 p.m.

1 stop7h 00m

C$ 646

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 20/5

6:30 a.m.-10:54 a.m.

1 stop4h 24m

Winnipeg

Fri 22/5

3:50 p.m.-10:55 p.m.

1 stop7h 05m

C$ 648

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 30/4

5:10 a.m.-11:52 a.m.

1 stop6h 42m

Winnipeg

Sat 2/5

8:45 a.m.-9:27 p.m.

1 stop12h 42m

C$ 648

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 20/5

6:30 a.m.-10:54 a.m.

1 stop4h 24m

Winnipeg

Sat 23/5

3:50 p.m.-10:55 p.m.

1 stop7h 05m

C$ 648

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 30/4

5:10 a.m.-11:52 a.m.

1 stop6h 42m

Winnipeg

Sun 3/5

2:00 p.m.-11:59 p.m.

1 stop9h 59m

C$ 648

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Tue 5/5

6:00 a.m.-10:56 a.m.

1 stop4h 56m

Winnipeg

Tue 12/5

3:50 p.m.-9:27 p.m.

1 stop5h 37m

C$ 648

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Tue 5/5

1:55 p.m.-12:55 a.m.

2 stops11h 00m

Winnipeg

Wed 6/5

7:00 a.m.-10:46 p.m.

2 stops15h 46m

C$ 672

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/3

Showing 1-10 of 51 resultsSorted by cheapest first
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Best time to book a flight from Wisconsin to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Wisconsin 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 Wisconsin to Winnipeg
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Winnipeg. 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 into for flights to Winnipeg from Wisconsin?

    For a flight from Wisconsin to Winnipeg, you will be flying into Winnipeg. Winnipeg (YWG) is just 7.3 km from the centre of the city.

  • How long is the flight from Wisconsin to Winnipeg?

    Airlines like WestJet, United Airlines, and Delta fly from Wisconsin to Winnipeg in about 4h 24m. The time it takes to get you to your destination can typically vary by up to 15h 21m. Airlines will cover a distance of 1051 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most popular routes from Wisconsin to Winnipeg?

    The most popular route from Wisconsin to Winnipeg is Chicago O'Hare Intl - Winnipeg. You may also consider Minneapolis St Paul - Winnipeg or Milwaukee-Mitchell - Winnipeg.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Wisconsin to Winnipeg 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

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk

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

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

Yes! Cheapflights helps users easily find flights from Wisconsin to Winnipeg with no change fees.

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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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