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$426+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 2/267:00 am
MKE
-
YWG
1 stop4h 57m
United Airlines
Mon 3/22:20 pm
YWG
-
MKE
1 stop8h 08m
United Airlines
Deal found 1/27$426
This Justfly.com deal was found by Cheapflights users on 1/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:54 pm
MKE
-
YWG
2 stops11h 01m
WestJet
Wed 6/176:40 am
YWG
-
MKE
1 stop4h 31m
WestJet
Deal found 1/28$434
This FlightHub deal was found by Cheapflights users on 1/27. 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 2/266:00 am
MKE
-
YWG
2 stops18h 35m
WestJet
Mon 3/211:53 am
YWG
-
MKE
1 stop6h 20m
WestJet
Deal found 1/27$442
This FlightHub deal was found by Cheapflights users on 1/27. 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 3/126:30 am
MKE
-
YWG
1 stop4h 31m
WestJet
Mon 3/165:00 am
YWG
-
MKE
2 stops16h 46m
WestJet
Deal found 1/27$446
This FlightHub deal was found by Cheapflights users on 1/27. 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 3/129:21 am
MKE
-
YWG
2 stops9h 48m
WestJet
Tue 3/316:45 am
YWG
-
MKE
2 stops11h 31m
WestJet
Deal found 1/27$448
This Priceline deal was found by Cheapflights users on 1/28. 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.
Wed 5/610:53 am
MKE
-
YWG
2 stops11h 17m
WestJet
Wed 6/176:40 am
YWG
-
MKE
1 stop4h 31m
WestJet
Deal found 1/28$451
This Delta deal was found by Cheapflights users on 1/28. 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 5/83:15 pm
MKE
-
YWG
1 stop8h 12m
Delta
Mon 6/158:50 am
YWG
-
MKE
1 stop7h 52m
Delta
Deal found 1/28$457
This Justfly.com deal was found by Cheapflights users on 1/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:45 am
MKE
-
YWG
2 stops18h 10m
WestJet
Wed 6/176:40 am
YWG
-
MKE
1 stop4h 31m
WestJet
Deal found 1/28$467
This FlightHub deal was found by Cheapflights users on 1/28. 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 2/1211:02 am
MKE
-
YWG
1 stop23h 59m
WestJet
Mon 2/165:00 am
YWG
-
MKE
2 stops15h 21m
WestJet
Deal found 1/28$470
This FlightHub deal was found by Cheapflights users on 1/28. 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 3/56:15 am
MKE
-
YWG
1 stop4h 46m
WestJet
Sun 3/88:05 pm
YWG
-
MKE
2 stops17h 23m
WestJet
Deal found 1/28$471
This Justfly.com deal was found by Cheapflights users on 1/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:54 pm
MKE
-
YWG
2 stops11h 01m
WestJet
Tue 6/166:15 am
YWG
-
MKE
2 stops9h 52m
WestJet
Deal found 1/28$472

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$426
(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 January 29, 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 3/9

6:00 am-11:57 am

1 stop5h 57m

Winnipeg

Wed 3/11

2:20 pm-8:45 pm

1 stop6h 25m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 3/12

6:30 am-11:01 am

1 stop4h 31m

Winnipeg

Tue 3/31

6:40 am-11:36 am

1 stop4h 56m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 3/19

5:00 am-11:57 am

1 stop6h 57m

Winnipeg

Sun 3/22

2:20 pm-9:50 pm

1 stop7h 30m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 3/5

6:15 am-11:01 am

1 stop4h 46m

Winnipeg

Sun 3/8

6:40 am-11:36 am

1 stop4h 56m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sun 4/5

6:50 am-11:52 am

1 stop5h 02m

Winnipeg

Fri 4/10

2:00 pm-6:47 pm

1 stop4h 47m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 3/4

7:00 am-11:57 am

1 stop4h 57m

Winnipeg

Fri 3/6

2:20 pm-8:45 pm

1 stop6h 25m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 2/26

7:00 am-11:57 am

1 stop4h 57m

Winnipeg

Mon 3/2

2:20 pm-10:28 pm

1 stop8h 08m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 3/12

6:00 am-11:57 am

1 stop5h 57m

Winnipeg

Mon 3/16

2:20 pm-8:45 pm

1 stop6h 25m

$426

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 3/12

6:30 am-11:01 am

1 stop4h 31m

Winnipeg

Mon 3/16

5:00 am-9:46 pm

2 stops16h 46m

$446

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Thu 2/26

6:00 am-12:35 am

2 stops18h 35m

Winnipeg

Mon 3/2

12:20 pm-9:51 pm

2 stops9h 31m

$456

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

  • 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 United Airlines and Delta fly from Milwaukee to Winnipeg in about 4h 31m. The time it takes to get you to your destination can typically vary by up to 1h 26m. 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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