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$434+ Cheap flights from Milwaukee (MKE) to Winnipeg (YWG)

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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Apr 14 — Apr 211
Tue 4/14
Tue 4/21
1 adult, Economy
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Cheap flight deals from Milwaukee to Winnipeg

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 March 15, 2026.

This FlightHub deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:59 pm
MKE
-
YWG
1 stop4h 36m
WestJet
Sat 4/185:20 pm
YWG
-
MKE
1 stop5h 26m
WestJet
Deal found 3/12$434
This FlightHub deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:20 am
MKE
-
YWG
2 stops7h 55m
WestJet
Fri 7/244:09 pm
YWG
-
MKE
1 stop17h 52m
WestJet
Deal found 3/14$444
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:10 am
MKE
-
YWG
1 stop6h 42m
United Airlines
Sat 5/22:00 pm
YWG
-
MKE
1 stop8h 03m
United Airlines
Deal found 3/10$450
This Priceline deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:15 pm
MKE
-
YWG
1 stop4h 54m
WestJet
Mon 9/147:00 am
YWG
-
MKE
2 stops9h 42m
WestJet
Deal found 3/12$453
This FlightHub deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:00 pm
MKE
-
YWG
1 stop11h 27m
WestJet
Mon 8/247:00 am
YWG
-
MKE
2 stops9h 42m
WestJet
Deal found 3/12$465
This FlightHub deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:00 am
MKE
-
YWG
2 stops14h 10m
WestJet
Sun 6/144:09 pm
YWG
-
MKE
1 stop3h 16m
WestJet
Deal found 3/10$469

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 March 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$434
(FlightHub)
Provider with most accurate pricing for Milwaukee-Mitchell-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Winnipeg flights.
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From Milwaukee-Mitchell to Winnipeg
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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 2,558,603 searches. Data last updated March 15, 2026.
Use the filters below to find and compare flights from Milwaukee to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sat 4/11

6:59 pm-11:35 pm

1 stop4h 36m

Winnipeg

Sat 4/18

5:20 pm-10:46 pm

1 stop5h 26m

$434

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 6/11

10:38 am-10:33 pm

1 stop11h 55m

Winnipeg

Sun 6/14

7:00 am-7:51 pm

1 stop12h 51m

$450

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 4/29

5:10 am-11:52 am

1 stop6h 42m

Winnipeg

Sat 5/2

2:00 pm-10:03 pm

1 stop8h 03m

$450

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 6/11

8:00 am-10:10 pm

2 stops14h 10m

Winnipeg

Sun 6/14

4:09 pm-7:25 pm

1 stop3h 16m

$469

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 4/29

5:48 pm-10:56 am

1 stop17h 08m

Winnipeg

Sat 5/2

5:20 pm-4:34 pm

1 stop23h 14m

$491

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Mon 4/20

5:48 pm-10:56 am

1 stop17h 08m

Winnipeg

Thu 4/23

5:20 pm-7:58 pm

1 stop26h 38m

$491

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sat 4/25

5:05 pm-2:25 pm

2 stops21h 20m

Winnipeg

Sat 5/2

7:00 am-10:13 am

2 stops27h 13m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Milwaukee-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Milwaukee-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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?

    Airlines like WestJet and United Airlines fly from Milwaukee to Winnipeg in about 4h 36m. The time it takes to get you to your destination can typically vary by up to 7h 19m. The distance between Milwaukee and Winnipeg is about 653 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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

Traveling to a place near Winnipeg?

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

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