$122 Find Cheap Flights from Canada to Wisconsin - Compare and Save

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Cheap Flights from Canada to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Minneapolis
Minneapolis
1h 31mNonstop
from $188per person
Chicago
Chicago
1h 55mNonstop
from $198per person
Madison
Madison
3h 52m2 stops
from $350per person
Milwaukee
Milwaukee
4h 06m2 stops
from $355per person
Duluth
Duluth
4h 42m2 stops
from $413per person
Wausau
Wausau
5h 55m3 stops
from $430per person
Appleton
Appleton
6h 35m2 stops
from $474per person
Green Bay
Green Bay
4h 24m2 stops
from $535per person
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Cheap Flights from Canada to Wisconsin

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Canada to Wisconsin

Tue, Oct 6 - Sat, Oct 10
Air Canada Logo
12:25 pm - 1:23 pmYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
1h 58mnonstop
Air Canada Logo
9:55 am - 12:40 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 45mnonstop
$198Air Canada
Tue, Oct 6 - Sat, Oct 10
Air Canada Logo
8:05 am - 9:00 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
1h 55mnonstop
Air Canada Logo
3:40 pm - 11:18 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
6h 38m1 stop Montreal Pierre Elliott Trudeau Intl
$201Air Canada
Fri, Oct 30 - Sat, Oct 31
United Airlines Logo
7:26 pm - 8:48 pmYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 22mnonstop
United Airlines Logo
7:03 am - 9:47 amORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 44mnonstop
$205United Airlines
Mon, Oct 26 - Fri, Oct 30
United Airlines Logo
6:45 am - 7:54 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 09mnonstop
United Airlines Logo
7:03 am - 9:47 amORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 44mnonstop
$205United Airlines
Thu, Oct 29 - Thu, Nov 5
American Airlines Logo
6:25 pm - 7:30 pmYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 05mnonstop
American Airlines Logo
9:42 am - 12:32 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 50mnonstop
$205American Airlines
Sat, Nov 21 - Tue, Nov 24
American Airlines Logo
7:09 am - 8:39 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 30mnonstop
American Airlines Logo
2:50 pm - 5:40 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 50mnonstop
$205American Airlines
Fri, Oct 30 - Tue, Nov 3
Multiple Airlines Logo
8:35 am - 9:44 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 09mnonstop
Multiple Airlines Logo
12:50 pm - 3:33 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 43mnonstop
$205Multiple Airlines
Fri, Oct 23 - Tue, Oct 27
Multiple Airlines Logo
8:50 am - 9:48 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
1h 58mnonstop
Multiple Airlines Logo
10:15 am - 12:52 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 37mnonstop
$205Multiple Airlines
Sat, Oct 31 - Fri, Nov 6
Porter Airlines Logo
10:35 am - 11:40 amYTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 05mnonstop
Porter Airlines Logo
6:20 pm - 9:06 pmORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 46mnonstop
$206Porter Airlines
Wed, Nov 11 - Sat, Nov 14
Porter Airlines Logo
4:35 pm - 5:40 pmYTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 05mnonstop
Porter Airlines Logo
12:20 pm - 3:06 pmORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 46mnonstop
$208Porter Airlines
Booking Insights

KAYAK's insights & trends for flights to Wisconsin

Get data-powered insights and trends for flights to Wisconsin to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Canada to Wisconsin?

The cheapest month for flights from Canada to Wisconsin is November, when tickets cost $217 (return) on average. On the other hand, the most expensive months are February and January, when the average cost of round-trip tickets is $457 and $443 respectively.

Find deals

Good to know

Low season

January

Cheapest flight

$122
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Vancouver to Minneapolis

FAQs for booking flights from Canada to Wisconsin

  • How does KAYAK find such low prices on flights from Canada to Wisconsin?

    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 Canada to Wisconsin.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Canada to Wisconsin 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 Canada to Wisconsin?

    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 from Canada to Wisconsin with an airline and back with another airline.

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

    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 from Canada to Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Canada to Wisconsin

 
Need help choosing which airline to fly with from Canada to Wisconsin? 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.
7.4
United AirlinesOverall score based on 10213 reviews
6.7Food
7.1Entertainment
7.7Boarding
8.1Crew
7.3Comfort
Airline reviews

Boarding was a complete mess. The whole system went down. People got wrong seat for the first half an hour.

2.0 MediocreYu Kin Chris, Aug 2026
Read more United Airlines reviews

Boarding was a complete mess. The whole system went down. People got wrong seat for the first half an hour.

Really delayed, no effort to support customers other than “sometimes we run late.”

The website check in was poor. Baggage fees were in US dollars but registered in Canadian dollars. The site would not accept my credit card. Scanning the passport was the worst. Someone from United needs to try the process. I’m not a novice with tech and I have to say this was a bad experience. Everything else was great.

We boarded the plane and were about to take off when we were notified that the tires had to be checked. Upon inspection, they were found to need replacement, so the entire plane had to be deboarded. After we exited the plane, United staff forced us to stay in the gate area by posting "Do Not Exit" signs on the doors connecting the gate area to the terminal. Many of us had already rebooked our flights and had no checked bags, but they told us we could not leave. This seemed inappropriate to hold people under false pretenses. When the agent told us we could leave, I asked them to please take down the "Do Not Exit" signs, as they were misleading. The agent refused, and I told them that it didn't feel right to hold people like that.

Friendly crew, but we were delayed for more than an hour and had to change planes due to maintenance issues.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

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