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Cheap flights from Milwaukee to Winnipeg from C$ 253

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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
27 Feb — 6 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Milwaukee to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Milwaukee to Winnipeg
Explore the most affordable flight options available from Milwaukee to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 January 2026.

Mon 9/36:00 a.m.
MKE
-
YWG
1 stop5h 57m
United Airlines
Wed 11/32:20 p.m.
YWG
-
MKE
1 stop4h 23m
United Airlines
Deal found 25/1C$ 567
Thu 26/26:00 a.m.
MKE
-
YWG
1 stop5h 57m
United Airlines
Mon 2/32:20 p.m.
YWG
-
MKE
1 stop8h 08m
United Airlines
Deal found 28/1C$ 582
Thu 26/211:15 a.m.
MKE
-
YWG
2 stops13h 20m
WestJet
Mon 2/311:53 a.m.
YWG
-
MKE
1 stop6h 20m
WestJet
Deal found 28/1C$ 604
Thu 12/36:30 a.m.
MKE
-
YWG
1 stop4h 31m
WestJet
Tue 31/312:20 p.m.
YWG
-
MKE
2 stops8h 56m
WestJet
Deal found 27/1C$ 610
Thu 12/36:15 a.m.
MKE
-
YWG
2 stops12h 54m
WestJet
Thu 19/36:45 a.m.
YWG
-
MKE
2 stops8h 31m
WestJet
Deal found 26/1C$ 633
Thu 12/211:02 a.m.
MKE
-
YWG
1 stop23h 59m
WestJet
Mon 16/25:00 a.m.
YWG
-
MKE
2 stops15h 21m
WestJet
Deal found 28/1C$ 642
Mon 3/812:00 p.m.
MKE
-
YWG
2 stops9h 25m
WestJet
Sat 8/87:00 a.m.
YWG
-
MKE
2 stops9h 42m
WestJet
Deal found 27/1C$ 655
Mon 3/83:15 p.m.
MKE
-
YWG
1 stop8h 12m
Delta
Sat 8/86:40 a.m.
YWG
-
MKE
1 stop7h 31m
Delta
Deal found 27/1C$ 666

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 28 January 2026.

Round-trip from

C$ 567

One-way from

C$ 253
United Airlines
  • United Airlines
  • 9/3-11/3
  • 2 total stops
  • 10h 20m total
  • Milwaukee to Winnipeg
Search Deals
United Airlines
  • United Airlines
  • 12/3
  • 1 total stop
  • 5h 57m 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 28 January 2026.
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

Mon 9/3

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

1 stop5h 57m

Winnipeg

Wed 11/3

2:20 p.m.-6:43 p.m.

1 stop4h 23m

C$ 567

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 12/3

6:30 a.m.-11:01 a.m.

1 stop4h 31m

Winnipeg

Thu 19/3

5:20 p.m.-9:16 p.m.

1 stop3h 56m

C$ 567

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 12/3

6:30 a.m.-11:01 a.m.

1 stop4h 31m

Winnipeg

Tue 31/3

6:40 a.m.-11:36 a.m.

1 stop4h 56m

C$ 582

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sun 5/4

6:50 a.m.-11:52 a.m.

1 stop5h 02m

Winnipeg

Fri 10/4

2:00 p.m.-6:47 p.m.

1 stop4h 47m

C$ 582

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 26/2

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

1 stop4h 57m

Winnipeg

Mon 2/3

2:20 p.m.-10:28 p.m.

1 stop8h 08m

C$ 582

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 12/3

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

1 stop5h 57m

Winnipeg

Mon 16/3

2:20 p.m.-8:45 p.m.

1 stop6h 25m

C$ 582

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 12/3

6:30 a.m.-11:01 a.m.

1 stop4h 31m

Winnipeg

Tue 31/3

12:20 p.m.-9:16 p.m.

2 stops8h 56m

C$ 610

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 12/3

6:30 a.m.-11:01 a.m.

1 stop4h 31m

Winnipeg

Mon 16/3

5:00 a.m.-9:46 p.m.

2 stops16h 46m

C$ 610

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 12/3

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

1 stop5h 57m

C$ 253

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 12/3

9:21 a.m.-7:09 p.m.

2 stops9h 48m

C$ 305

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

Showing 1-10 of 11 results
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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.

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 4h 31m. Fly via United Airlines or Delta to get the fastest option. There are 1051 km between Milwaukee and Winnipeg. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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.

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

See prices for flight routes from nearby airports that may be better suited for you.
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Can Cheapflights find flights from Milwaukee to Winnipeg with no change fees?

Need flexible booking options for your flight to Winnipeg from Milwaukee? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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