$386+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Nov 3 — Nov 101
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Winnipeg with Cheapflights
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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
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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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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 4, 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 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/2. 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.
Tue 11/174:40 pm -
2 stops20h 10m
Thu 11/196:35 am -
1 stop11h 28m
Deal found 10/2![Multiple Airlines logo]()
$845
This oojo deal was found by Cheapflights users on 9/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:49 am -
2 stops27h 01m
Sun 11/15:00 am -
2 stops27h 40m
Deal found 9/29![WestJet logo]()
$884
This oojo deal was found by Cheapflights users on 10/1. 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.
Mon 10/266:47 pm -
2 stops29h 57m
Fri 10/308:55 pm -
2 stops17h 14m
Deal found 10/1![WestJet logo]()
$885
This oojo deal was found by Cheapflights users on 10/2. 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.
Tue 11/176:45 pm -
2 stops25h 05m
Thu 11/195:00 am -
2 stops12h 11m
Deal found 10/2![WestJet logo]()
$891
This United Airlines deal was found by Cheapflights users on 10/2. 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 11/175:00 am -
1 stop7h 23m
Thu 11/192:15 pm -
1 stop4h 43m
Deal found 10/2![United Airlines logo]()
$911
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Mon 10/265:00 am -
1 stop7h 23m
Fri 10/308:40 am -
1 stop12h 19m
Deal found 10/4![United Airlines logo]()
$948
This oojo deal was found by Cheapflights users on 10/1. 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.
Sun 11/157:00 am -
2 stops36h 50m
Sun 11/229:35 am -
2 stops12h 25m
Deal found 10/1![WestJet logo]()
$969
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 4, 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 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/2. 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.
Tue 11/174:40 pm -
2 stops20h 10m
Thu 11/196:35 am -
1 stop11h 28m
Deal found 10/2![Multiple Airlines logo]()
$845
This oojo deal was found by Cheapflights users on 9/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:49 am -
2 stops27h 01m
Sun 11/15:00 am -
2 stops27h 40m
Deal found 9/29![WestJet logo]()
$884
This United Airlines deal was found by Cheapflights users on 10/3. 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 1/1212:45 pm -
1 stop5h 43m
Wed 1/137:00 am -
1 stop5h 05m
Deal found 10/3![United Airlines logo]()
$911
This oojo deal was found by Cheapflights users on 10/1. 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.
Mon 10/266:47 pm -
2 stops29h 57m
Fri 10/308:55 pm -
2 stops17h 14m
Deal found 10/1![WestJet logo]()
$885
This United Airlines deal was found by Cheapflights users on 10/2. 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 11/175:00 am -
1 stop7h 23m
Thu 11/192:15 pm -
1 stop4h 43m
Deal found 10/2![United Airlines logo]()
$911
This United Airlines deal was found by Cheapflights users on 10/1. 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 11/158:30 am -
1 stop12h 27m
Sun 11/228:40 am -
1 stop8h 24m
Deal found 10/1![United Airlines logo]()
$948
This United Airlines deal was found by Cheapflights users on 9/29. 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 10/306:48 am -
1 stop5h 35m
Sun 11/12:15 pm -
1 stop8h 00m
Deal found 9/29![United Airlines logo]()
$948
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Mon 10/265:00 am -
1 stop7h 23m
Fri 10/308:40 am -
1 stop12h 19m
Deal found 10/4![United Airlines logo]()
$948
Last-minute flights from Milwaukee to WinnipegDiscover last-minute flight deals from Milwaukee to Winnipeg. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Winnipeg. Data last updated October 4, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 10/1. 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.
Mon 10/266:47 pm -
2 stops29h 57m
Fri 10/308:55 pm -
2 stops17h 14m
Deal found 10/1![WestJet logo]()
$885
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Mon 10/265:00 am -
1 stop7h 23m
Fri 10/308:40 am -
1 stop12h 19m
Deal found 10/4![United Airlines logo]()
$948
This oojo deal was found by Cheapflights users on 9/29. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:49 am -
2 stops27h 01m
Sun 11/15:00 am -
2 stops27h 40m
Deal found 9/29![WestJet logo]()
$884
This oojo deal was found by Cheapflights users on 10/1. 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.
Sun 11/157:00 am -
2 stops36h 50m
Sun 11/229:35 am -
2 stops12h 25m
Deal found 10/1![WestJet logo]()
$969
This Kiwi.com deal was found by Cheapflights users on 10/2. 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.
Tue 11/174:40 pm -
2 stops20h 10m
Thu 11/196:35 am -
1 stop11h 28m
Deal found 10/2![Multiple Airlines logo]()
$845
This oojo deal was found by Cheapflights users on 10/2. 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.
Tue 11/176:45 pm -
2 stops25h 05m
Thu 11/195:00 am -
2 stops12h 11m
Deal found 10/2![WestJet logo]()
$891
This United Airlines deal was found by Cheapflights users on 10/2. 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 11/175:00 am -
1 stop7h 23m
Thu 11/192:15 pm -
1 stop4h 43m
Deal found 10/2![United Airlines logo]()
$911
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 4, 2026.
Search for one-way flight options from Milwaukee to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/1. 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.
Sun 11/154:40 pm -
3 stops19h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 10/1. 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 11/158:30 am -
1 stop12h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![United Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 9/30. 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 11/148:30 am -
1 stop12h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$477
This WestJet deal was found by Cheapflights users on 9/30. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/148:10 am -
2 stops16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![WestJet logo]()
$501
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 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $845 (Kiwi.com) |
One-way from | $386 (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 4, 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
Sun 11/15
4:40 pm-12:45 pm
3 stops19h 05m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$386
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Sun 11/15
8:30 am-9:57 pm
1 stop12h 27m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$425
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Sat 11/14
8:30 am-9:57 pm
1 stop12h 27m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$477
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Sat 11/14
8:10 am-1:44 am
2 stops16h 34m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$501
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 11/17
4:40 pm-1:50 pm
2 stops20h 10m
Winnipeg
Thu 11/19
6:35 am-5:03 pm
1 stop11h 28m
$845
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Fri 10/30
10:49 am-1:50 pm
2 stops27h 01m
Winnipeg
Sun 11/1
5:00 am-7:40 am
2 stops27h 40m
$884
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Mon 10/26
6:47 pm-12:44 am
2 stops29h 57m
Winnipeg
Fri 10/30
8:55 pm-2:09 pm
2 stops17h 14m
$885
Quickest round-trip
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 1/12
12:45 pm-7:28 pm
1 stop5h 43m
Winnipeg
Wed 1/13
7:00 am-11:05 am
1 stop5h 05m
$911
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 11/17
5:00 am-1:23 pm
1 stop7h 23m
Winnipeg
Thu 11/19
2:15 pm-5:58 pm
1 stop4h 43m
$911
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Sun 11/15
8:30 am-9:57 pm
1 stop12h 27m
Winnipeg
Sun 11/22
8:40 am-4:04 pm
1 stop8h 24m
$948
Showing 1-10 of 12 resultsSorted 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 4, 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.
Food
7.2
Boarding
8.1
Overall
7.8
Comfort
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Boarding
8.1
Overall
7.8
Comfort
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Boarding
8.1
Overall
7.8
Comfort
7.8
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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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Milwaukee and Winnipeg flights
Browse other Milwaukee and Winnipeg flight options. Last updated on October 4, 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 4, 2026.
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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 4, 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 4, 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 |