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$432+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Milwaukee to Winnipeg

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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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 1/216:00 amMKE - YWG
1 stop5h 57mUnited Airlines
Wed 1/212:20 pmYWG - MKE
1 stop4h 33mUnited Airlines
Deal found 12/10$432
This FlightHub deal was found by Cheapflights users on 12/10. 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.
Wed 1/211:18 pmMKE - YWG
2 stops11h 17mWestJet
Thu 1/225:21 pmYWG - MKE
1 stop4h 09mWestJet
Deal found 12/10$484
This Delta deal was found by Cheapflights users on 12/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/223:15 pmMKE - YWG
1 stop8h 12mDelta
Tue 5/265:38 pmYWG - MKE
1 stop3h 44mDelta
Deal found 12/11$500
This United Airlines deal was found by Cheapflights users on 12/10. 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 1/217:00 amMKE - YWG
1 stop4h 57mUnited Airlines
Thu 1/222:20 pmYWG - MKE
1 stop7h 39mUnited Airlines
Deal found 12/10$432
This United Airlines deal was found by Cheapflights users on 12/9. 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.
Tue 1/135:00 amMKE - YWG
1 stop6h 57mUnited Airlines
Wed 1/142:20 pmYWG - MKE
1 stop6h 28mUnited Airlines
Deal found 12/9$432
This FlightHub deal was found by Cheapflights users on 12/10. 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.
Fri 1/166:59 pmMKE - YWG
1 stop16h 04mWestJet
Sun 1/188:05 pmYWG - MKE
2 stops12h 43mWestJet
Deal found 12/10$489
This FlightHub deal was found by Cheapflights users on 12/11. 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 1/151:18 pmMKE - YWG
2 stops11h 17mWestJet
Sun 1/188:05 pmYWG - MKE
2 stops12h 43mWestJet
Deal found 12/11$493
This FlightHub deal was found by Cheapflights users on 12/11. 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.
Fri 5/226:25 pmMKE - YWG
2 stops19h 18mWestJet
Tue 5/2612:40 pmYWG - MKE
1 stop4h 02mWestJet
Deal found 12/11$516

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$432
(United Airlines)
Provider with most accurate pricing for Milwaukee-Mitchell-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Winnipeg flights.
Search Deals
From Milwaukee-Mitchell 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 2,558,603 searches. Data last updated December 12, 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 1/21

6:00 am-11:57 am

1 stop5h 57m

Winnipeg

Wed 1/21

2:20 pm-6:53 pm

1 stop4h 33m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 1/21

7:00 am-11:57 am

1 stop4h 57m

Winnipeg

Thu 1/22

2:20 pm-9:59 pm

1 stop7h 39m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Tue 1/13

5:00 am-11:57 am

1 stop6h 57m

Winnipeg

Wed 1/14

2:20 pm-8:48 pm

1 stop6h 28m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 1/21

1:18 pm-12:35 am

2 stops11h 17m

Winnipeg

Thu 1/22

5:21 pm-9:30 pm

1 stop4h 09m

$484

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 1/16

6:59 pm-11:03 am

1 stop16h 04m

Winnipeg

Sun 1/18

8:05 pm-8:48 am

2 stops12h 43m

$489

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 1/15

1:18 pm-12:35 am

2 stops11h 17m

Winnipeg

Sun 1/18

8:05 pm-8:48 am

2 stops12h 43m

$493

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 5/22

3:15 pm-11:27 pm

1 stop8h 12m

Winnipeg

Tue 5/26

5:38 pm-9:22 pm

1 stop3h 44m

$500

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 5/22

6:25 pm-1:43 pm

2 stops19h 18m

Winnipeg

Tue 5/26

12:40 pm-4:42 pm

1 stop4h 02m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Compare providers for flights from Milwaukee to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milwaukee to Winnipeg in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Milwaukee-Winnipeg flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-Winnipeg flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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 $89). Flying from Milwaukee to Winnipeg in November is currently the most expensive (average of $614). 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.

What is the cheapest time of day to fly from MKE to YWG?

Find hourly flight availability from Milwaukee to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Milwaukee to Winnipeg in the afternoon. If you’re flexible enough to do this you can expect to save up to 23% on your trip compared to booking a flight in the evening.

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 United Airlines fly from Milwaukee to Winnipeg in about 5h 57m. The time it takes to get you to your destination can typically vary by up to . The distance between Milwaukee and Winnipeg is about 653 mi.

  • 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 $89). Flying from Milwaukee to Winnipeg in November is currently the most expensive (average of $614). 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

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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