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Cheap flights from Milwaukee to Winnipeg from C$ 596

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 13/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Milwaukee to Winnipeg

Enter your travel dates to find the best prices.

Best flights from Milwaukee to Winnipeg
Discover carefully curated flight deals from Milwaukee to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 December 2025.

Wed 21/16:00 a.m.MKE - YWG
1 stop5h 57mUnited Airlines
Wed 21/12:20 p.m.YWG - MKE
1 stop4h 33mUnited Airlines
Deal found 10/12C$ 596
Wed 21/11:18 p.m.MKE - YWG
2 stops11h 17mWestJet
Thu 22/15:21 p.m.YWG - MKE
1 stop4h 09mWestJet
Deal found 10/12C$ 667
Fri 22/53:15 p.m.MKE - YWG
1 stop8h 12mDelta
Tue 26/55:38 p.m.YWG - MKE
1 stop3h 44mDelta
Deal found 11/12C$ 690
Wed 21/17:00 a.m.MKE - YWG
1 stop4h 57mUnited Airlines
Thu 22/12:20 p.m.YWG - MKE
1 stop7h 39mUnited Airlines
Deal found 10/12C$ 596
Tue 13/15:00 a.m.MKE - YWG
1 stop6h 57mUnited Airlines
Wed 14/12:20 p.m.YWG - MKE
1 stop6h 28mUnited Airlines
Deal found 9/12C$ 596
Thu 15/13:59 p.m.MKE - YWG
1 stop19h 04mWestJet
Sun 18/18:05 p.m.YWG - MKE
2 stops12h 43mWestJet
Deal found 11/12C$ 674
Fri 16/16:59 p.m.MKE - YWG
1 stop16h 04mWestJet
Sun 18/18:05 p.m.YWG - MKE
2 stops12h 43mWestJet
Deal found 10/12C$ 674
Fri 22/56:25 p.m.MKE - YWG
2 stops19h 18mWestJet
Tue 26/512:40 p.m.YWG - MKE
1 stop4h 02mWestJet
Deal found 11/12C$ 712

Find flight deals from Milwaukee to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Winnipeg (YWG). 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 12 December 2025.

Round-trip from

C$ 596
United Airlines
  • United Airlines
  • 13/1-14/1
  • 2 total stops
  • 13h 25m total
  • Milwaukee to Winnipeg
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 12 December 2025.
Use the filters below to find and compare flights from Milwaukee to Winnipeg that are best for you.

Fly from

Milwaukee

Fly to

Winnipeg

Route

Depart

Return

Price

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 21/1

6:00 a.m.-11:57 a.m.

1 stop5h 57m

Winnipeg

Wed 21/1

2:20 p.m.-6:53 p.m.

1 stop4h 33m

C$ 596

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 21/1

7:00 a.m.-11:57 a.m.

1 stop4h 57m

Winnipeg

Thu 22/1

2:20 p.m.-9:59 p.m.

1 stop7h 39m

C$ 596

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Tue 13/1

5:00 a.m.-11:57 a.m.

1 stop6h 57m

Winnipeg

Wed 14/1

2:20 p.m.-8:48 p.m.

1 stop6h 28m

C$ 596

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 21/1

1:18 p.m.-12:35 a.m.

2 stops11h 17m

Winnipeg

Thu 22/1

5:21 p.m.-9:30 p.m.

1 stop4h 09m

C$ 667

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 15/1

3:59 p.m.-11:03 a.m.

1 stop19h 04m

Winnipeg

Sun 18/1

8:05 p.m.-8:48 a.m.

2 stops12h 43m

C$ 674

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 16/1

6:59 p.m.-11:03 a.m.

1 stop16h 04m

Winnipeg

Sun 18/1

8:05 p.m.-8:48 a.m.

2 stops12h 43m

C$ 674

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 22/5

3:15 p.m.-11:27 p.m.

1 stop8h 12m

Winnipeg

Tue 26/5

5:38 p.m.-9:22 p.m.

1 stop3h 44m

C$ 690

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 22/5

6:25 p.m.-1:43 p.m.

2 stops19h 18m

Winnipeg

Tue 26/5

12:40 p.m.-4:42 p.m.

1 stop4h 02m

C$ 712

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Best time to book a flight from Milwaukee to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Milwaukee 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 Milwaukee to Winnipeg

What is the cheapest month to book a flight from Milwaukee to Winnipeg?

Currently, May is the cheapest month in which you can book a flight from Milwaukee to Winnipeg (average of C$ 123). Flying from Milwaukee to Winnipeg in November is currently the most expensive (average of C$ 847). 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.

Related info for your journey

Find useful and relevant information for your journey from Milwaukee to Winnipeg. 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 Milwaukee to Winnipeg?

    There are many flights that can get you from Milwaukee to Winnipeg in 5h 57m. Fly via United Airlines to get the fastest option. There are 1051 km between Milwaukee and Winnipeg.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee 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.

  • What is the cheapest month to book a flight from Milwaukee to Winnipeg?

    Currently, May is the cheapest month in which you can book a flight from Milwaukee to Winnipeg (average of C$ 123). Flying from Milwaukee to Winnipeg in November is currently the most expensive (average of C$ 847). 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

Travelling to a place near Winnipeg?

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

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Alternative routes for Milwaukee to Winnipeg

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

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