C$ 104 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 11/12. 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

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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
TorontodirectC$ 262
Ottawa
Ottawa1 stopC$ 447
Toronto
TorontodirectC$ 262
Ottawa
Ottawa1 stopC$ 447

Cheap Flights from Midway to Canada

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

Recent round-trip flight deals from Midway to Canada

Wed, 19 Nov - Sat, 22 Nov
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
11:00 a.m. - 11:50 a.m.YTZ-MDW
1h 50mdirect
C$ 262Porter Airlines
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Wed, 12 Nov - Sun, 16 Nov
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
C$ 265Porter Airlines
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Wed, 3 Dec - Sun, 7 Dec
Multiple Airlines Logo
2:49 p.m. - 11:12 a.m.MDW-YVR
22h 23m1 stop
Multiple Airlines Logo
11:00 p.m. - 9:52 a.m.YVR-MDW
8h 52m1 stop
C$ 272Multiple Airlines
Find Deal
Fri, 12 Dec - Sun, 14 Dec
Multiple Airlines Logo
8:42 p.m. - 11:12 a.m.MDW-YVR
16h 30m1 stop
Multiple Airlines Logo
11:00 p.m. - 10:12 p.m.YVR-MDW
21h 12m1 stop
C$ 293Multiple Airlines
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Fri, 5 Dec - Sun, 7 Dec
Delta Logo
1:14 p.m. - 5:15 p.m.MDW-YYZ
3h 01m1 stop
Delta Logo
12:13 p.m. - 6:00 p.m.YYZ-MDW
6h 47m1 stop
C$ 325Delta
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Sat, 14 Feb - Tue, 17 Feb
Delta Logo
5:59 p.m. - 11:12 p.m.MDW-YUL
4h 13m1 stop
Delta Logo
6:00 a.m. - 12:35 p.m.YUL-MDW
7h 35m1 stop
C$ 329Delta
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Wed, 12 Nov - Thu, 13 Nov
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
Air Transat Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
C$ 337Air Transat
Find Deal
Thu, 13 Nov - Sun, 16 Nov
Air Transat Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
Air Transat Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
C$ 340Air Transat
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Wed, 26 Nov - Wed, 3 Dec
WestJet Logo
9:41 a.m. - 11:39 p.m.MDW-YYZ
12h 58m2 stops
WestJet Logo
6:12 p.m. - 9:54 a.m.YYZ-MDW
16h 42m1 stop
C$ 412WestJet
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Tue, 25 Nov - Tue, 2 Dec
WestJet Logo
1:47 p.m. - 11:21 p.m.MDW-YYZ
8h 34m1 stop
WestJet Logo
6:30 p.m. - 9:54 a.m.YYZ-MDW
16h 24m2 stops
C$ 419WestJet
Find Deal
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Canada from Chicago Midway Airport found in the last 72 hours was to Toronto, at C$ 218 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 C$ 218.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 306 on average.

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 C$ 249 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is C$ 522 and C$ 522 respectively.

Good to know

Low seasonMarch
Best time to beat the crowds but there is an average 67% increase in price.
Most popular time to fly and prices are also 32% lower on average.

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 travellers 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.

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

    The cheapest time of day to fly to Canada is generally in the morning, when round-trip flights cost C$ 365 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Canada is generally in the afternoon, which is peak travel time and where the average cost of a ticket is C$ 472.

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 C$ 260 one-way - C$ 396 round-trip

Reviews of the 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 384 reviews
8.2Boarding
8.6Crew
7.0Entertainment
8.0Comfort
7.6Food
Airline reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

8.0 ExcellentPilar, Oct 2025FLL - YOW
Read more Porter Airlines reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

All good the seats a little tight and no I pad screen

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

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