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$457+ Cheap flights from Milwaukee (MKE) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
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 July 29, 2026.

This Justfly.com deal was found by Cheapflights users on 7/25. 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 9/86:47 pm
MKE
-
YWG
2 stops19h 38m
WestJet
Tue 9/155:44 pm
YWG
-
MKE
1 stop17h 39m
WestJet
Deal found 7/25$676
This Justfly.com deal was found by Cheapflights users on 7/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/93:15 pm
MKE
-
YWG
1 stop8h 14m
WestJet
Fri 12/116:35 am
YWG
-
MKE
1 stop7h 38m
WestJet
Deal found 7/27$680
This Justfly.com deal was found by Cheapflights users on 7/25. 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.
Wed 9/1610:00 am
MKE
-
YWG
2 stops12h 10m
WestJet
Sat 9/265:44 pm
YWG
-
MKE
1 stop17h 39m
WestJet
Deal found 7/25$687
This Justfly.com deal was found by Cheapflights users on 7/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:00 am
MKE
-
YWG
1 stop4h 08m
WestJet
Mon 9/283:58 pm
YWG
-
MKE
1 stop3h 36m
WestJet
Deal found 7/29$697
This United Airlines deal was found by Cheapflights users on 7/25. 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 9/86:00 am
MKE
-
YWG
1 stop5h 52m
United Airlines
Tue 9/152:00 pm
YWG
-
MKE
1 stop7h 00m
United Airlines
Deal found 7/25$715
This oojo deal was found by Cheapflights users on 7/26. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:30 am
MKE
-
YWG
2 stops15h 40m
WestJet
Mon 9/287:00 am
YWG
-
MKE
2 stops14h 09m
WestJet
Deal found 7/26$724
This oojo deal was found by Cheapflights users on 7/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:35 am
MKE
-
YWG
2 stops15h 20m
WestJet
Tue 10/275:00 am
YWG
-
MKE
2 stops15h 06m
WestJet
Deal found 7/27$732

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 July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$676
(Justfly.com)

One-way from

$457
(American 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
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One-way flight 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 July 29, 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

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Tue 9/8

6:47 pm-2:25 pm

2 stops19h 38m

Winnipeg

Tue 9/15

5:44 pm-11:23 am

1 stop17h 39m

$676

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Tue 9/8

6:00 am-11:52 am

1 stop5h 52m

Winnipeg

Tue 9/15

2:00 pm-9:00 pm

1 stop7h 00m

$715

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 12/9

7:00 am-7:15 pm

2 stops12h 15m

Winnipeg

Fri 12/11

10:55 am-11:42 am

2 stops24h 47m

$733

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Fri 9/25

6:30 am-3:08 pm

1 stop8h 38m

Winnipeg

Mon 9/28

3:58 pm-9:09 pm

1 stop5h 11m

$736
Quickest round-trip

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sat 10/3

7:18 am-12:37 pm

1 stop5h 19m

Winnipeg

Tue 10/6

2:00 pm-7:10 pm

1 stop5h 10m

$743

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Sat 9/26

1:28 pm-12:55 am

2 stops11h 27m

Winnipeg

Mon 9/28

7:00 am-9:09 pm

2 stops14h 09m

$743
Cheapest one-way
Quickest one-way

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 8/5

7:25 am-7:54 pm

2 stops12h 29m

$457

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 8/5

3:59 pm-4:52 pm

1 stop24h 53m

$585

MilwaukeeWinnipeg

MKE - YWG

MKEYWG

Milwaukee-Mitchell

Wed 8/5

6:02 am-5:25 pm

3 stops35h 23m

$717

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated July 29, 2026.
Read reviews from past customers who have flown Delta and United Airlines from Milwaukee to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,494 reviews

Comfort

7.8

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,494 reviews
Delta
7.8
Good
8,494 reviews

Comfort

7.8

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
10,052 reviews
Delta
7.8
Good
8,494 reviews

Comfort

7.8

Food

7.2

Entertainment

7.8

Crew

8.5

Overall

7.8

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 5h 52m. The time it takes to get you to your destination can typically vary by up to 13h 46m. The distance between Milwaukee and Winnipeg is about 653 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Milwaukee to Winnipeg round-trip?

    United Airlines, at $170, was found to be the cheapest airline from Milwaukee to Winnipeg. An alternate airline flying to your destination would be Delta.

  • 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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Alternative routes for Milwaukee to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
Minneapolis to Winnipeg flights
Madison to Winnipeg flights
Duluth to Winnipeg flights

Top 2 airlines flying from Milwaukee to Winnipeg

Discover the top 2 airlines that operate flights from Milwaukee to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$170Average$185FlexibilityNo cancel feeOn-time69%
DeltaCheapest$193Average$640FlexibilityNo cancel feeOn-timeN/A

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