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Cheap flights from Milwaukee to Winnipeg from C$ 549

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 31/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
28 Nov — 5 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap 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 29 October 2025.

Round-trip from

C$ 604
United Airlines
  • United Airlines
  • 10/3-11/3
  • 2 total stops
  • 15h 07m total
  • Milwaukee to Winnipeg
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Find 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 29 October 2025.

Wed 31/123:00 p.m.MKE - YWG
1 stop9h 43mMultiple Airlines
Wed 7/17:30 a.m.YWG - MKE
2 stops29h 21mMultiple Airlines
Deal found 29/10C$ 549
Wed 31/123:00 p.m.MKE - YWG
1 stop9h 43mMultiple Airlines
Tue 6/112:10 p.m.YWG - MKE
2 stops30h 35mMultiple Airlines
Deal found 29/10C$ 566
Wed 31/123:00 p.m.MKE - YWG
1 stop9h 43mMultiple Airlines
Thu 8/17:30 a.m.YWG - MKE
1 stop29h 06mMultiple Airlines
Deal found 29/10C$ 597
Fri 26/127:08 a.m.MKE - YWG
1 stop4h 49mUnited Airlines
Tue 6/12:20 p.m.YWG - MKE
1 stop6h 28mUnited Airlines
Deal found 29/10C$ 604
Mon 29/126:25 a.m.MKE - YWG
1 stop5h 20mDelta
Wed 7/15:21 p.m.YWG - MKE
1 stop4h 15mDelta
Deal found 29/10C$ 653
Mon 29/126:25 a.m.MKE - YWG
1 stop5h 20mDelta
Thu 8/16:35 a.m.YWG - MKE
2 stops14h 19mDelta
Deal found 29/10C$ 667
Sun 28/124:04 p.m.MKE - YWG
1 stop7h 40mDelta
Sun 4/17:30 a.m.YWG - MKE
1 stop9h 31mDelta
Deal found 29/10C$ 708
Wed 31/123:00 p.m.MKE - YWG
1 stop9h 43mMultiple Airlines
Sun 4/17:30 a.m.YWG - MKE
2 stops27h 43mMultiple Airlines
Deal found 29/10C$ 711
Sun 28/124:04 p.m.MKE - YWG
1 stop7h 40mDelta
Wed 7/16:35 a.m.YWG - MKE
2 stops9h 51mDelta
Deal found 29/10C$ 722
Fri 26/127:08 a.m.MKE - YWG
1 stop4h 49mUnited Airlines
Mon 5/15:30 a.m.YWG - MKE
2 stops13h 23mUnited Airlines
Deal found 29/10C$ 725
Tue 30/128:30 a.m.MKE - YWG
2 stops13h 14mUnited Airlines
Mon 5/15:30 a.m.YWG - MKE
2 stops13h 23mUnited Airlines
Deal found 29/10C$ 741

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 29 October 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

Sat 27/12

7:08 a.m.-11:57 a.m.

1 stop4h 49m

Winnipeg

Tue 6/1

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

1 stop4h 33m

C$ 604

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 31/12

6:25 a.m.-11:45 a.m.

1 stop5h 20m

Winnipeg

Wed 7/1

5:21 p.m.-9:36 p.m.

1 stop4h 15m

C$ 604

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Tue 10/3

6:00 a.m.-11:39 a.m.

1 stop5h 39m

Winnipeg

Wed 11/3

2:15 p.m.-10:43 p.m.

1 stop8h 28m

C$ 604

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 8/4

2:30 p.m.-8:48 p.m.

1 stop6h 18m

Winnipeg

Wed 15/4

2:15 p.m.-10:09 p.m.

1 stop7h 54m

C$ 604

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sat 10/1

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

1 stop6h 57m

Winnipeg

Sun 25/1

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

1 stop7h 39m

C$ 604

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sun 28/12

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

1 stop6h 57m

Winnipeg

Thu 8/1

2:20 p.m.-10:56 p.m.

1 stop8h 36m

C$ 604

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sun 1/2

7:07 p.m.-11:38 p.m.

1 stop4h 31m

Winnipeg

Wed 18/2

6:40 a.m.-12:31 p.m.

2 stops5h 51m

C$ 616

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 23/1

1:31 p.m.-6:06 p.m.

3 stops28h 35m

Winnipeg

Sun 25/1

10:55 a.m.-12:36 p.m.

3 stops25h 41m

C$ 658

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Mon 29/12

6:25 a.m.-11:45 a.m.

1 stop5h 20m

Winnipeg

Wed 7/1

6:35 a.m.-4:26 p.m.

2 stops9h 51m

C$ 667

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/10

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$ 127). Flying from Milwaukee to Winnipeg in November is currently the most expensive (average of C$ 858). 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 4h 49m. 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$ 127). Flying from Milwaukee to Winnipeg in November is currently the most expensive (average of C$ 858). 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

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?

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