C$ 92 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 12/4. 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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Flight Deals

Best Canada Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
TorontodirectC$ 240
Ottawa
Ottawa1 stopC$ 345
Toronto
TorontodirectC$ 240
Ottawa
Ottawa1 stopC$ 345

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

Fri, 10 Apr - Fri, 17 Apr
Porter Airlines Logo
4:05 p.m. - 6:47 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.
YTZ
-
MDW
1h 50mdirect
C$ 240Porter Airlines
Sat, 28 Mar - Mon, 30 Mar
Porter Airlines Logo
12:45 p.m. - 3:27 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 242Porter Airlines
Wed, 22 Apr - Wed, 29 Apr
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:25 a.m. - 10:15 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 243Porter Airlines
Sat, 18 Apr - Sun, 19 Apr
Porter Airlines Logo
12:55 p.m. - 3:37 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.
YTZ
-
MDW
1h 50mdirect
C$ 244Porter Airlines
Sat, 28 Mar - Mon, 30 Mar
Porter Airlines Logo
12:45 p.m. - 3:27 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 246Porter Airlines
Thu, 2 Apr - Sun, 5 Apr
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
Porter Airlines Logo
9:25 a.m. - 10:15 a.m.
YTZ
-
MDW
1h 50mdirect
C$ 247Porter Airlines
Fri, 29 May - Sun, 7 Jun
Delta Logo
6:36 p.m. - 10:59 p.m.
MDW
-
YYZ
3h 23m
1 stop
Delta Logo
6:00 a.m. - 8:42 a.m.
YYZ
-
MDW
3h 42m
1 stop
C$ 337Delta
Mon, 27 Apr - Fri, 1 May
Delta Logo
1:24 p.m. - 10:56 p.m.
MDW
-
YYZ
8h 32m
1 stop
Delta Logo
12:16 p.m. - 5:58 p.m.
YYZ
-
MDW
6h 42m
1 stop
C$ 350Delta
Thu, 2 Apr - Thu, 9 Apr
Delta Logo
6:34 p.m. - 10:39 p.m.
MDW
-
YYZ
3h 05m
1 stop
Delta Logo
6:20 a.m. - 8:53 a.m.
YYZ
-
MDW
3h 33m
1 stop
C$ 365Delta
Wed, 29 Apr - Mon, 4 May
Multiple Airlines Logo
6:10 a.m. - 7:10 p.m.
MDW
-
YVR
15h 00m
2 stops
Multiple Airlines Logo
10:55 p.m. - 10:19 p.m.
YVR
-
MDW
21h 24m
1 stop
C$ 410Multiple Airlines
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$ 248 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$ 248.

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 morning, when round-trip flights cost C$ 335 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Canada is generally in the evening, which is peak travel time and where the average cost of a ticket is C$ 341.

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 C$ 395, 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 C$ 243 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is C$ 600 and C$ 389 respectively.

Good to know

Low seasonJanuary
Best time to beat the crowds (27% less expensive on average)
Most popular time to fly (12% more expensive 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.

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$ 213 one-way - C$ 289 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 423 reviews
8.0Comfort
8.2Boarding
7.6Food
7.0Entertainment
8.6Crew
Airline reviews

The flight was a little delayed but check in was easy and boarding was quick. Luggage was quickly available and everything worked great.

10.0 ExcellentIngelwood, Feb 2026
CUN - YOW
Read more Porter Airlines reviews

The flight was a little delayed but check in was easy and boarding was quick. Luggage was quickly available and everything worked great.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

The flight booking code given by Kayak was not the correct one used by the airline. I had to call to get the correct one. It was never sent to me. Totally unacceptable!

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

Much roomer than air Canada! Great flight for the price. No complaints

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

As a first time flyer with Porter I was happy with the service and comfort of the airline.

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Other than wifi no on board entertainment. Will use them again, roomier seats than other airlines and snacks and beverages, better than average

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

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

Information on your arrival and departure airports