$211 Find Cheap Flights from Canada to Madison - Compare and Save

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Cheap Flights from Canada to Madison

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

Recent round-trip flight deals from Canada to Madison

Mon, Dec 14 - Tue, Dec 15
United Airlines Logo
2:50 pm - 10:23 pmYVR  Vancouver Intl-MSN Madison Truax Field
6h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
6:30 am - 12:45 pmMSN  Madison Truax Field-YVR Vancouver Intl
7h 15m1 stop Chicago O'Hare Intl
$378United Airlines
Mon, Dec 14 - Tue, Dec 15
United Airlines Logo
2:50 pm - 10:23 pmYVR  Vancouver Intl-MSN Madison Truax Field
6h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
6:30 am - 12:45 pmMSN  Madison Truax Field-YVR Vancouver Intl
7h 15m1 stop Chicago O'Hare Intl
$439United Airlines
Mon, Dec 14 - Tue, Dec 15
United Airlines Logo
2:50 pm - 10:23 pmYVR  Vancouver Intl-MSN Madison Truax Field
6h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
6:30 am - 12:45 pmMSN  Madison Truax Field-YVR Vancouver Intl
7h 15m1 stop Chicago O'Hare Intl
$453United Airlines
Wed, Dec 9 - Wed, Dec 16
Multiple Airlines Logo
7:15 am - 5:24 pmYYZ  Toronto Pearson Intl-MSN Madison Truax Field
11h 09m1 stop Fort Myers SW Florida Intl
Multiple Airlines Logo
10:38 am - 10:55 pmMSN  Madison Truax Field-YYZ Toronto Pearson Intl
11h 17m2 stops Tampa Fort Lauderdale
$462Multiple Airlines
Mon, Dec 14 - Tue, Dec 15
United Airlines Logo
2:50 pm - 10:23 pmYVR  Vancouver Intl-MSN Madison Truax Field
6h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
8:49 am - 10:19 pmMSN  Madison Truax Field-YVR Vancouver Intl
14h 30m2 stops Denver Intl San Francisco
$470United Airlines
Mon, Dec 14 - Tue, Dec 15
Alaska Airlines Logo
6:40 pm - 8:14 amYVR  Vancouver Intl-MSN Madison Truax Field
12h 34m2 stops Seattle/Tacoma Intl Chicago O'Hare Intl
Alaska Airlines Logo
11:33 am - 11:44 pmMSN  Madison Truax Field-YVR Vancouver Intl
13h 11m2 stops Chicago O'Hare Intl Seattle/Tacoma Intl
$472Alaska Airlines
Mon, Dec 14 - Tue, Dec 15
Alaska Airlines Logo
6:40 pm - 8:14 amYVR  Vancouver Intl-MSN Madison Truax Field
12h 34m2 stops Seattle/Tacoma Intl Chicago O'Hare Intl
Alaska Airlines Logo
11:33 am - 11:44 pmMSN  Madison Truax Field-YVR Vancouver Intl
13h 11m2 stops Chicago O'Hare Intl Seattle/Tacoma Intl
$473Alaska Airlines
Mon, Dec 14 - Tue, Dec 15
Alaska Airlines Logo
6:40 pm - 8:14 amYVR  Vancouver Intl-MSN Madison Truax Field
12h 34m2 stops Seattle/Tacoma Intl Chicago O'Hare Intl
Alaska Airlines Logo
11:33 am - 11:44 pmMSN  Madison Truax Field-YVR Vancouver Intl
13h 11m2 stops Chicago O'Hare Intl Seattle/Tacoma Intl
$474Alaska Airlines
Mon, Dec 14 - Tue, Dec 15
United Airlines Logo
2:50 pm - 10:23 pmYVR  Vancouver Intl-MSN Madison Truax Field
6h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
4:15 pm - 1:43 pmMSN  Madison Truax Field-YVR Vancouver Intl
22h 28m2 stops Denver Intl San Francisco
$478United Airlines
Tue, Jan 26 - Sat, Jan 30
United Airlines Logo
2:10 pm - 11:15 pmYHZ  Halifax Intl-MSN Madison Truax Field
11h 05m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
6:05 am - 1:24 pmMSN  Madison Truax Field-YHZ Halifax Intl
5h 19m1 stop Newark
$495United Airlines
Booking Insights

KAYAK's insights & trends for flights to Madison

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

What is the cheapest flight to Madison?

In the last 5 days, the cheapest flight deal to Madison was found on the route from Vancouver, at $378 return. The most popular connection is from Toronto to Madison and KAYAK users have found round-trip deals for as low as $516 in the last 5 days.

Good to know

Low season

September

Cheapest flight

$211
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Vancouver to Madison

FAQs - booking Madison flights

  • What is the cheapest flight to Madison?

    In the last 5 days, the cheapest flight deal to Madison was found on the route from Vancouver, at $378 return. The most popular connection is from Toronto to Madison and KAYAK users have found round-trip deals for as low as $516 in the last 5 days.

  • How far is Madison Truax Field Airport from central Madison?

    The city center of Madison is 5 miles from Madison Truax Field Airport.

  • What is the name of Madison’s airport?

    Madison is served by Madison Truax Field Airport, also commonly referred to as Truax Field. The airport code is MSN.

  • How does KAYAK find such low prices on flights to Madison?

    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 to Madison.

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

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

  • What is the Hacker Fare option on flights to Madison?

    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 Madison 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 to Madison?

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

  • How many direct flights to Madison are there each week?

    Each week there are around 1,344 direct flights from within Canada to Madison. The most common day for departures is Sunday, with 17% of flights taking off on this day.

Top tips for finding cheap flights to Madison

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Madison flight deals.

Reviews of the top airline flying from Canada to Madison

 
Need help choosing which airline to fly with to Madison? 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.
7.3
United AirlinesOverall score based on 10451 reviews
7.1Entertainment
8.1Crew
6.7Food
7.3Comfort
7.7Boarding
Airline reviews

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

4.0 OkayJoseph, Oct 2026
Read more United Airlines reviews

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

Very efficient. Economy is what economy is. Wish it had been direct. Excellent setup in Newark for commuters and access to charging stations and wifi Flight could’ve had free wifi

My flight was cancelled and United Airlines could not rebook or help. My whole trip was then cancelled and I could not go to the funeral I needed to get to.

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.”

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. .

Traveling to a place near Madison?

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