$84 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 4/15. 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

Cheap Flights from Midway to Canada

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
Torontononstop$216
Calgary
Calgary1 stop$283
Halifax
Halifax2 stops$335
Ottawa
Ottawa1 stop$342
Winnipeg
Winnipeg1 stop$423
Québec City
Québec City1 stop$489
St. John's
St. John's2 stops$490
Saskatoon
Saskatoon2 stops$665
Thunder Bay
Thunder Bay2 stops$475
Toronto
Torontononstop$216
Calgary
Calgary1 stop$283
Halifax
Halifax2 stops$335
Ottawa
Ottawa1 stop$342
Winnipeg
Winnipeg1 stop$423
Québec City
Québec City1 stop$489
St. John's
St. John's2 stops$490
Saskatoon
Saskatoon2 stops$665
Thunder Bay
Thunder Bay2 stops$475

Book Cheap Midway to Canada Plane Tickets

 
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

Mon, Apr 13 - Thu, Apr 16
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
$204Porter Airlines
Fri, Apr 17 - Sun, Apr 19
Porter Airlines Logo
4:05 pm - 10:45 pm
MDW
-
YUL
5h 40m
1 stop
Porter Airlines Logo
9:50 am - 3:20 pm
YUL
-
MDW
6h 30m
1 stop
$212Porter Airlines
Thu, Apr 23 - Mon, Apr 27
Porter Airlines Logo
11:00 am - 4:30 pm
MDW
-
YUL
4h 30m
1 stop
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
$213Porter Airlines
Mon, Apr 13 - Thu, Apr 16
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
$214Porter Airlines
Sun, Apr 19 - Mon, Apr 27
Porter Airlines Logo
4:05 pm - 10:45 pm
MDW
-
YUL
5h 40m
1 stop
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
$215Porter Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
7:34 pm - 11:00 am
MDW
-
YYC
16h 26m
1 stop
Multiple Airlines Logo
7:00 am - 10:14 pm
YYC
-
MDW
14h 14m
2 stops
$283Multiple Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
7:34 pm - 11:00 am
MDW
-
YYC
16h 26m
1 stop
Multiple Airlines Logo
7:00 am - 6:37 pm
YYC
-
MDW
10h 37m
1 stop
$285Multiple Airlines
Tue, Jun 2 - Mon, Jun 8
Delta Logo
9:23 am - 10:57 pm
MDW
-
YYC
14h 34m
2 stops
Delta Logo
6:35 am - 1:07 pm
YYC
-
MDW
5h 32m
1 stop
$305Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
1:59 pm - 8:30 pm
MDW
-
YYC
7h 31m
1 stop
Delta Logo
6:45 am - 5:56 pm
YYC
-
MDW
10h 11m
1 stop
$306Delta
Sat, Apr 11 - Mon, Apr 13
WestJet Logo
7:20 pm - 11:35 pm
MDW
-
YWG
4h 15m
1 stop
WestJet Logo
5:00 am - 5:58 pm
YWG
-
MDW
12h 58m
2 stops
$592WestJet
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 $82 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 $82.

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 $257 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 in the evening, which is peak travel time and where the average cost of a ticket is $258.

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 $256, 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 $179 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is $442 and $287 respectively.

Good to know

Low seasonJanuary
Cheapest flight$83
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Chicago Midway Airport to Montreal

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.

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 $106 one-way - $196 round-trip

Reviews of the top airlines 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
7.6Food
8.2Boarding
7.0Entertainment
8.6Crew
8.0Comfort
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

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

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

Information on your arrival and departure airports