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$393+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$393
(Kiwi.com)
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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Find 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:00 pmMKE - YWG
1 stop9h 43mMultiple Airlines
Wed 1/77:30 amYWG - MKE
2 stops29h 21mMultiple Airlines
Deal found 10/29$393
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:00 pmMKE - YWG
1 stop9h 43mMultiple Airlines
Tue 1/612:10 pmYWG - MKE
2 stops30h 35mMultiple Airlines
Deal found 10/29$405
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:00 pmMKE - YWG
1 stop9h 43mMultiple Airlines
Thu 1/87:30 amYWG - MKE
1 stop29h 06mMultiple Airlines
Deal found 10/29$427
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 12/267:08 amMKE - YWG
1 stop4h 49mUnited Airlines
Tue 1/62:20 pmYWG - MKE
1 stop6h 28mUnited Airlines
Deal found 10/29$432
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/296:25 amMKE - YWG
1 stop5h 20mDelta
Wed 1/75:21 pmYWG - MKE
1 stop4h 15mDelta
Deal found 10/29$467
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/296:25 amMKE - YWG
1 stop5h 20mDelta
Thu 1/86:35 amYWG - MKE
2 stops14h 19mDelta
Deal found 10/29$477
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 12/284:04 pmMKE - YWG
1 stop7h 40mDelta
Sun 1/47:30 amYWG - MKE
1 stop9h 31mDelta
Deal found 10/29$507
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:00 pmMKE - YWG
1 stop9h 43mMultiple Airlines
Sun 1/47:30 amYWG - MKE
2 stops27h 43mMultiple Airlines
Deal found 10/29$509
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 12/284:04 pmMKE - YWG
1 stop7h 40mDelta
Wed 1/76:35 amYWG - MKE
2 stops9h 51mDelta
Deal found 10/29$517
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 12/267:08 amMKE - YWG
1 stop4h 49mUnited Airlines
Mon 1/55:30 amYWG - MKE
2 stops13h 23mUnited Airlines
Deal found 10/29$519
This United Airlines deal was found by Cheapflights users on 10/29. 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 12/308:30 amMKE - YWG
2 stops11h 04mUnited Airlines
Wed 1/75:30 amYWG - MKE
2 stops10h 13mUnited Airlines
Deal found 10/29$530

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 October 29, 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 12/27

7:08 am-11:57 am

1 stop4h 49m

Winnipeg

Tue 1/6

2:20 pm-6:53 pm

1 stop4h 33m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 12/31

6:25 am-11:45 am

1 stop5h 20m

Winnipeg

Wed 1/7

5:21 pm-9:36 pm

1 stop4h 15m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Tue 3/10

6:00 am-11:39 am

1 stop5h 39m

Winnipeg

Wed 3/11

2:15 pm-10:43 pm

1 stop8h 28m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sun 2/1

7:07 pm-11:38 pm

1 stop4h 31m

Winnipeg

Wed 2/18

6:40 am-2:13 pm

1 stop7h 33m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 4/8

2:30 pm-8:48 pm

1 stop6h 18m

Winnipeg

Wed 4/15

2:15 pm-10:09 pm

1 stop7h 54m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sat 1/10

5:00 am-11:57 am

1 stop6h 57m

Winnipeg

Sun 1/25

2:20 pm-9:59 pm

1 stop7h 39m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sun 12/28

5:00 am-11:57 am

1 stop6h 57m

Winnipeg

Thu 1/8

2:20 pm-10:56 pm

1 stop8h 36m

$432

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Mon 12/29

6:25 am-11:45 am

1 stop5h 20m

Winnipeg

Wed 1/7

5:21 pm-9:36 pm

1 stop4h 15m

$467

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 1/23

1:31 pm-6:06 pm

3 stops28h 35m

Winnipeg

Sun 1/25

10:55 am-12:36 pm

3 stops25h 41m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 October.
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 $91). 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 October 29, 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 4h 49m. 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 $91). 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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