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$58 Find Cheap Flights from Chicago Midway Airport to Canada

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Canada departing on 5/21. 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.
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Best Canada Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Toronto
Torontononstop$145
Calgary
Calgary1 stop$251
Halifax
Halifax2 stops$321
Ottawa
Ottawa1 stop$218
Québec City
Québec City1 stop$406
Winnipeg
Winnipeg1 stop$346
St. John's
St. John's2 stops$419
Saskatoon
Saskatoon1 stop$338
Thunder Bay
Thunder Bay1 stop$348

Cheap Flight Deals from Midway to Canada (MDW-CA0)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Canada 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.

Recent round-trip flight deals from Midway to Canada

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Canada.
Discover the best prices for you by selecting your travel dates on KAYAK.
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Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$145Porter Airlines
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Thu, May 15 - Sun, May 18
Porter Airlines Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$146Porter Airlines
Find Deal
Fri, Jun 20 - Sun, Jun 22
Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$162
Find Deal
Sat, Jun 7 - Sat, Jun 14
Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$168
Find Deal
Sat, Jun 7 - Sat, Jun 14
Air Transat Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$196Air Transat
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Sat, Jun 7 - Tue, Jun 10
Delta Logo
1:55 pm - 11:14 pmMDW-YYZ
8h 19m1 stop
Delta Logo
10:11 am - 12:29 pmYYZ-MDW
3h 18m1 stop
$233Delta
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Sat, Jun 7 - Sat, Jun 14
Delta Logo
9:16 am - 5:15 pmMDW-YYZ
6h 59m1 stop
Delta Logo
6:30 am - 8:40 amYYZ-MDW
3h 10m1 stop
$241Delta
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Thu, May 15 - Sun, May 18
Air Transat Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$282Air Transat
Find Deal
Thu, Aug 14 - Sun, Aug 17
WestJet Logo
12:48 pm - 11:55 pmMDW-YYZ
10h 07m1 stop
WestJet Logo
1:04 pm - 5:40 pmYYZ-MDW
5h 36m1 stop
$312WestJet
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Sat, Jun 7 - Thu, Jun 12
WestJet Logo
9:20 am - 6:31 pmMDW-YYZ
8h 11m1 stop
WestJet Logo
1:04 pm - 5:40 pmYYZ-MDW
5h 36m1 stop
$333WestJet
Find Deal
Fri, Jun 6 - Fri, Jun 13

KAYAK's insights & trends for Midway to Canada flights

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

What is the cheapest Chicago Midway Airport to Canada flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Canada.
The cheapest ticket to Canada from Chicago Midway Airport found in the last 72 hours was to Toronto, at $193 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Toronto Island Airport (YTZ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $193.

What is the cheapest time of day to fly to Canada?

The average price for all round-trip flights from Chicago Midway Airport to Canada depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Canada is generally in the evening, when round-trip flights cost $293 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Canada is generally at night, which is peak travel time and where the average cost of a ticket is $360.

Can I save money by flying with a layover from Chicago Midway Airport to Canada?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of $524, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to Canada?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Canada, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Canada is July, when tickets cost $242 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is $381 and $363 respectively.
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Good to know

Low season

March

High season

April

Cheapest flight

$58
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago Midway Airport to Toronto Island

FAQs - booking Canada flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Canada?

    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 Chicago Midway Airport to Canada.

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

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

    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 Chicago Midway Airport to Canada 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 Chicago Midway Airport to Canada?

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

See more FAQs

Top tips for finding cheap flights to Canada

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Toronto $133 one-way - $227 round-trip

Top airline flying from Midway to Canada

Need help choosing which airline to fly with from Midway to Canada? 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.
8.0
Porter AirlinesOverall score based on 284 reviews
8.1Comfort
8.2Boarding
8.8Crew
7.0Entertainment
7.6Food
Airline reviews

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

10.0 ExcellentDiane, Apr 2025YYZ - TPA
Read more Porter Airlines reviews

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Everything you need to know for your flight from Midway to Canada

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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