$348+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Oct 13 — Oct 201
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
Cheapest
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 September 13, 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 September 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/276:30 am -
1 stop5h 18m
Tue 11/38:05 pm -
2 stops37h 11m
Deal found 9/11![Multiple Airlines logo]()
$703
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 12/105:33 pm -
1 stop31h 11m
Mon 12/147:00 am -
2 stops11h 02m
Deal found 9/11![Multiple Airlines logo]()
$712
This oojo deal was found by Cheapflights users on 9/9. 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.
Sat 10/249:35 am -
2 stops10h 45m
Sat 10/318:55 pm -
2 stops25h 18m
Deal found 9/9![WestJet logo]()
$714
This oojo deal was found by Cheapflights users on 9/9. 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 10/306:30 am -
2 stops19h 14m
Sun 11/17:55 pm -
2 stops25h 18m
Deal found 9/9![WestJet logo]()
$733
This oojo deal was found by Cheapflights users on 9/11. 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 10/2710:36 am -
2 stops14h 08m
Tue 11/35:00 am -
2 stops14h 30m
Deal found 9/11![WestJet logo]()
$736
This oojo deal was found by Cheapflights users on 9/11. 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 12/1010:55 am -
2 stops8h 55m
Mon 12/145:00 am -
2 stops16h 51m
Deal found 9/11![WestJet logo]()
$764
This oojo deal was found by Cheapflights users on 9/8. 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 10/235:45 pm -
2 stops26h 15m
Fri 10/308:05 pm -
2 stops14h 08m
Deal found 9/8![WestJet logo]()
$775
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 September 13, 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 September 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/276:30 am -
1 stop5h 18m
Tue 11/38:05 pm -
2 stops37h 11m
Deal found 9/11![Multiple Airlines logo]()
$703
This oojo deal was found by Cheapflights users on 9/9. 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 10/306:30 am -
2 stops19h 14m
Sun 11/17:55 pm -
2 stops25h 18m
Deal found 9/9![WestJet logo]()
$733
This oojo deal was found by Cheapflights users on 9/11. 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 10/2710:36 am -
2 stops14h 08m
Tue 11/35:00 am -
2 stops14h 30m
Deal found 9/11![WestJet logo]()
$736
Last-minute flights from Milwaukee to WinnipegDiscover last-minute flight deals from Milwaukee to Winnipeg. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Winnipeg. Data last updated September 13, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 9/8. 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 10/235:45 pm -
2 stops26h 15m
Fri 10/308:05 pm -
2 stops14h 08m
Deal found 9/8![WestJet logo]()
$775
This oojo deal was found by Cheapflights users on 9/9. 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.
Sat 10/249:35 am -
2 stops10h 45m
Sat 10/318:55 pm -
2 stops25h 18m
Deal found 9/9![WestJet logo]()
$714
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/276:30 am -
1 stop5h 18m
Tue 11/38:05 pm -
2 stops37h 11m
Deal found 9/11![Multiple Airlines logo]()
$703
This oojo deal was found by Cheapflights users on 9/11. 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 10/2710:36 am -
2 stops14h 08m
Tue 11/35:00 am -
2 stops14h 30m
Deal found 9/11![WestJet logo]()
$736
This oojo deal was found by Cheapflights users on 9/9. 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 10/306:30 am -
2 stops19h 14m
Sun 11/17:55 pm -
2 stops25h 18m
Deal found 9/9![WestJet logo]()
$733
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 September 13, 2026.
Search for one-way flight options from Milwaukee to Winnipeg. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/293:03 pm -
3 stops42h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/8. 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 9/295:03 am -
2 stops14h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![American Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 9/8. 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 9/295:00 am -
1 stop7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$383
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 September 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $703 (Kiwi.com) |
One-way from | $348 (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 September 13, 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
Tue 9/29
3:03 pm-9:20 am
3 stops42h 17m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$348
Quickest round-trip
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 9/29
5:00 am-12:37 pm
1 stop7h 37m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$383
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 10/27
6:30 am-11:48 am
1 stop5h 18m
Winnipeg
Tue 11/3
8:05 pm-9:16 am
2 stops37h 11m
$703
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Fri 10/30
6:30 am-1:44 am
2 stops19h 14m
Winnipeg
Sun 11/1
7:55 pm-9:13 pm
2 stops25h 18m
$733
MilwaukeeWinnipeg
MKE Milwaukee-Mitchell - YWG Winnipeg
MKEYWG
Milwaukee-Mitchell
Tue 10/27
10:36 am-12:44 am
2 stops14h 08m
Winnipeg
Tue 11/3
5:00 am-7:30 pm
2 stops14h 30m
$736
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 September 13, 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.
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Overall
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 September 13, 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 September 13, 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 September 13, 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 September 13, 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 |