MKE - YWG

$209 Find Cheap Flights from Milwaukee to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Winnipeg departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Winnipeg, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$435
WestJet
Thu 6/4Mon 6/8
MKE - YWG • 2 stops
Cheapest one-way
$209
WestJet
Sat 5/30
MKE - YWG • 2 stops
Top airlines
Cheapest • from $435 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Milwaukee and Winnipeg. You'll need at least 1 connection.
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We hope you love your trip to Winnipeg!
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Flight Deals

Cheap Flights from Milwaukee to Winnipeg (MKE-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Winnipeg

Thu, Jun 4 - Mon, Jun 8
WestJet Logo
12:15 pm - 9:40 pm
MKE
-
YWG
9h 25m
2 stops
WestJet Logo
6:40 am - 11:17 am
YWG
-
MKE
4h 37m
1 stop
$435WestJet
Mon, May 25 - Fri, May 29
WestJet Logo
5:48 pm - 11:26 pm
MKE
-
YWG
5h 38m
1 stop
WestJet Logo
6:00 am - 4:51 pm
YWG
-
MKE
10h 51m
2 stops
$438WestJet
Wed, Jun 24 - Thu, Jul 2
WestJet Logo
9:37 am - 12:55 am
MKE
-
YWG
15h 18m
2 stops
WestJet Logo
6:00 am - 6:19 pm
YWG
-
MKE
12h 19m
2 stops
$440WestJet
Wed, Jun 24 - Thu, Jul 2
WestJet Logo
3:58 pm - 11:56 am
MKE
-
YWG
19h 58m
1 stop
WestJet Logo
6:00 am - 6:19 pm
YWG
-
MKE
12h 19m
2 stops
$444WestJet
Wed, Jun 24 - Thu, Jul 2
WestJet Logo
12:07 pm - 11:56 am
MKE
-
YWG
23h 49m
1 stop
WestJet Logo
5:41 pm - 9:28 pm
YWG
-
MKE
3h 47m
1 stop
$464WestJet
Mon, Jul 20 - Fri, Jul 24
WestJet Logo
12:07 pm - 11:40 pm
MKE
-
YWG
11h 33m
2 stops
WestJet Logo
7:00 am - 6:00 pm
YWG
-
MKE
11h 00m
2 stops
$465WestJet
Thu, Jun 4 - Mon, Jun 8
WestJet Logo
12:15 pm - 9:40 pm
MKE
-
YWG
9h 25m
2 stops
WestJet Logo
10:30 pm - 6:19 pm
YWG
-
MKE
19h 49m
2 stops
$467WestJet
Thu, May 21 - Mon, May 25
WestJet Logo
12:15 pm - 9:45 am
MKE
-
YWG
21h 30m
2 stops
WestJet Logo
6:40 am - 11:20 am
YWG
-
MKE
4h 40m
1 stop
$468WestJet
Mon, Jul 20 - Fri, Jul 24
WestJet Logo
6:40 pm - 2:25 pm
MKE
-
YWG
19h 45m
2 stops
WestJet Logo
7:00 am - 6:00 pm
YWG
-
MKE
11h 00m
2 stops
$474WestJet
Thu, May 21 - Mon, May 25
WestJet Logo
6:30 am - 5:15 pm
MKE
-
YWG
10h 45m
2 stops
WestJet Logo
10:30 pm - 4:51 pm
YWG
-
MKE
18h 21m
2 stops
$475WestJet
Booking Insights

KAYAK's insights & trends for Milwaukee to Winnipeg flights

Get data-powered insights and trends into flights from Milwaukee to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Milwaukee to Winnipeg?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Milwaukee to Winnipeg were found on WestJet ($435) and Delta ($616).

Good to know

Cheapest flight$209
Flight from Milwaukee to Winnipeg

When to book flights from Milwaukee to Winnipeg

Are your dates flexible? Find out the best times to travel from Milwaukee to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Milwaukee to Winnipeg

  • What is the cheapest flight from Milwaukee to Winnipeg?

    In the last 3 days, the lowest price for a flight from Milwaukee to Winnipeg was $209 for a one-way ticket and $435 for a round-trip.

  • Do I need a passport to fly between Milwaukee and Winnipeg?

    Yes

  • Which aircraft models fly most regularly from Milwaukee to Winnipeg?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Milwaukee to Winnipeg?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Milwaukee and Winnipeg, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Milwaukee to Winnipeg, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Milwaukee to Winnipeg are Delta and United Airlines. With an average price for the route of $640 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $205 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Milwaukee to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Milwaukee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Milwaukee with another airline. Booking your flights between Milwaukee and YWG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Milwaukee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Milwaukee to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Winnipeg. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milwaukee to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8456 reviews
7.9Comfort
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

10.0 ExcellentIrmara, May 2026
MCO - BOS
Read more Delta reviews

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

Some crew were unfriendly or in some cases just straight up rude.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

Entertainment kept turning itself off. Gave up on watching a movie.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Not United Airlines' fault. It's ORL airport's fault.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Everything you need to know for your flight from Milwaukee to Winnipeg

Information on your arrival and departure airports