$350+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Winnipeg with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Milwaukee to Winnipeg
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Best
Last-minute
One-way
Cheapest flights from Milwaukee to WinnipegExplore 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 25, 2026.
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 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/24. 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 12/87:00 am -
1 stop5h 23m
Tue 12/153:15 pm -
1 stop4h 33m
Deal found 10/24![United Airlines logo]()
$912
This American Airlines deal was found by Cheapflights users on 10/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:00 am -
2 stops16h 57m
Tue 12/157:00 am -
2 stops17h 59m
Deal found 10/24![American Airlines logo]()
$930
This United Airlines deal was found by Cheapflights users on 10/20. 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 12/45:00 am -
1 stop7h 23m
Fri 12/113:15 pm -
1 stop7h 40m
Deal found 10/20![United Airlines logo]()
$944
This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:00 am -
2 stops16h 57m
Fri 12/117:00 am -
2 stops17h 59m
Deal found 10/20![American Airlines logo]()
$948
This Delta deal was found by Cheapflights users on 10/20. 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 12/412:53 pm -
2 stops10h 46m
Fri 12/115:24 pm -
1 stop5h 07m
Deal found 10/20![Delta logo]()
$953
This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:04 am -
2 stops16h 48m
Fri 11/137:00 am -
2 stops25h 48m
Deal found 10/20![American Airlines logo]()
$964
This Mytrip deal was found by Cheapflights users on 10/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/83:50 pm -
3 stops18h 57m
Tue 12/159:35 pm -
3 stops22h 39m
Deal found 10/24![Multiple Airlines logo]()
$988
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/122:35 pm -
1 stop6h 22m
Fri 11/139:40 am -
1 stop8h 24m
Deal found 10/20![United Airlines logo]()
$1,023
This oojo deal was found by Cheapflights users on 10/20. 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.
Thu 11/1210:53 am -
1 stop12h 40m
Fri 11/136:00 am -
2 stops27h 50m
Deal found 10/20![WestJet logo]()
$1,040
Best flights from Milwaukee to WinnipegDiscover 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 October 25, 2026.
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 October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Sat 1/98:40 am -
1 stop9h 48m
Sun 1/108:00 am -
1 stop7h 00m
Deal found 10/21![United Airlines logo]()
$874
This FlightHub deal was found by Cheapflights users on 10/21. 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 1/93:15 pm -
1 stop20h 35m
Mon 1/116:00 am -
2 stops11h 07m
Deal found 10/21![WestJet logo]()
$924
This Mytrip deal was found by Cheapflights users on 10/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/83:50 pm -
3 stops18h 57m
Tue 12/159:35 pm -
3 stops22h 39m
Deal found 10/24![Multiple Airlines logo]()
$988
This United Airlines deal was found by Cheapflights users on 10/20. 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 1/129:20 am -
1 stop9h 08m
Wed 1/138:00 am -
1 stop7h 00m
Deal found 10/20![United Airlines logo]()
$911
This United Airlines deal was found by Cheapflights users on 10/24. 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 12/87:00 am -
1 stop5h 23m
Tue 12/153:15 pm -
1 stop4h 33m
Deal found 10/24![United Airlines logo]()
$912
Last-minute flights from Milwaukee to WinnipegDiscover last-minute flight deals from Milwaukee to Winnipeg. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Winnipeg. Data last updated October 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/20. 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 10/308:00 am -
2 stops13h 14m
Sun 11/13:15 pm -
1 stop8h 00m
Deal found 10/20![United Airlines logo]()
$1,279
This Delta deal was found by Cheapflights users on 10/20. 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 10/303:20 pm -
1 stop7h 59m
Sun 11/11:38 pm -
1 stop6h 52m
Deal found 10/20![Delta logo]()
$1,298
This oojo deal was found by Cheapflights users on 10/23. 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 10/3010:49 am -
2 stops30h 36m
Sun 11/110:00 am -
2 stops10h 30m
Deal found 10/23![WestJet logo]()
$1,322
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Sun 11/86:47 am -
1 stop5h 36m
Sun 11/87:55 pm -
2 stops18h 37m
Deal found 10/20![United Airlines logo]()
$1,153
This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:04 am -
2 stops16h 48m
Fri 11/137:00 am -
2 stops25h 48m
Deal found 10/20![American Airlines logo]()
$964
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/122:35 pm -
1 stop6h 22m
Fri 11/139:40 am -
1 stop8h 24m
Deal found 10/20![United Airlines logo]()
$1,023
This oojo deal was found by Cheapflights users on 10/20. 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.
Thu 11/1210:53 am -
1 stop12h 40m
Fri 11/136:00 am -
2 stops27h 50m
Deal found 10/20![WestJet logo]()
$1,040
One-way flights from Milwaukee to WinnipegSearch for one-way flight options from Milwaukee to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Milwaukee to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Thu 11/266:00 am -
2 stops14h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/265:00 am -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$410
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $874 (United Airlines) |
One-way from | $350 (Kiwi.com) |
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 7,457,451 searches. Data last updated October 25, 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
Cheapest round-trip
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Thu 11/26
6:00 am-9:45 pm
2 stops14h 45m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$350
Quickest round-trip
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Thu 11/26
5:00 am-1:23 pm
1 stop7h 23m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$410
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Sat 1/9
8:40 am-7:28 pm
1 stop9h 48m
Winnipeg
Sun 1/10
8:00 am-2:00 pm
1 stop7h 00m
$874
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 1/12
9:20 am-7:28 pm
1 stop9h 08m
Winnipeg
Wed 1/13
8:00 am-2:00 pm
1 stop7h 00m
$911
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 12/8
7:00 am-1:23 pm
1 stop5h 23m
Winnipeg
Tue 12/15
3:15 pm-6:48 pm
1 stop4h 33m
$912
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Sat 1/9
3:15 pm-12:50 pm
1 stop20h 35m
Winnipeg
Mon 1/11
6:00 am-4:07 pm
2 stops11h 07m
$924
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 12/8
3:50 pm-11:47 am
3 stops18h 57m
Winnipeg
Tue 12/15
9:35 pm-7:14 pm
3 stops22h 39m
$988
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.
MKE-YWG
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 October 25, 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.
Crew
8.5
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Crew
8.5
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Crew
8.5
Entertainment
7.8
Overall
7.8
Food
7.2
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
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.
Traveling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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Alternative routes for Milwaukee to Winnipeg
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Complete your trip
Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Winnipeg by cabin class
Find flights from Milwaukee to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Winnipeg flights
Browse other Milwaukee and Winnipeg flight options. Last updated on October 25, 2026.
Other flights from Milwaukee
Browse through other flights departing from Milwaukee. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$170 | Average$185 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$193 | Average$640 | FlexibilityNo cancel fee | On-timeN/A |