$79 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 2/1. 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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Cheap Flights from Midway to Canada

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
Torontononstop$194
Calgary
Calgary1 stop$228
Halifax
Halifax1 stop$256
Ottawa
Ottawa1 stop$310
Québec City
Québec City1 stop$433
Winnipeg
Winnipeg2 stops$243
St. John's
St. John's2 stops$578
Saskatoon
Saskatoon2 stops$947
Thunder Bay
Thunder Bay1 stop$491
Toronto
Torontononstop$194
Calgary
Calgary1 stop$228
Halifax
Halifax1 stop$256
Ottawa
Ottawa1 stop$310
Québec City
Québec City1 stop$433
Winnipeg
Winnipeg2 stops$243
St. John's
St. John's2 stops$578
Saskatoon
Saskatoon2 stops$947
Thunder Bay
Thunder Bay1 stop$491

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

Wed, Feb 4 - Thu, Feb 12
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
$194Porter Airlines
Sat, Jan 31 - Sun, Feb 1
Porter Airlines Logo
12:45 pm - 3:27 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
$197Porter Airlines
Mon, Feb 23 - Mon, Mar 2
Multiple Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Multiple Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
$199Multiple Airlines
Mon, Feb 23 - Mon, Mar 2
Multiple Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Multiple Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
$200Multiple Airlines
Wed, Jan 28 - Thu, Feb 5
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
$202Porter Airlines
Thu, Mar 12 - Sun, Mar 15
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
$203Porter Airlines
Thu, Jan 22 - Sun, Jan 25
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pm
YTZ
-
MDW
1h 50mnonstop
$204Porter Airlines
Thu, Feb 5 - Sun, Feb 8
Delta Logo
9:33 am - 4:12 pm
MDW
-
YYZ
5h 39m1 stop
Delta Logo
6:00 am - 8:52 am
YYZ
-
MDW
3h 52m1 stop
$236Delta
Mon, Feb 2 - Sun, Feb 8
Delta Logo
6:35 pm - 11:12 pm
MDW
-
YUL
3h 37m1 stop
Delta Logo
6:00 am - 12:46 pm
YUL
-
MDW
7h 46m1 stop
$237Delta
Thu, Feb 5 - Sun, Feb 8
Delta Logo
9:53 am - 3:59 pm
MDW
-
YYZ
5h 06m1 stop
Delta Logo
6:30 am - 11:05 am
YYZ
-
MDW
5h 35m1 stop
$237Delta
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 $139 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 $139.

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 $347, 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 March, when tickets cost $97 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is $371 and $287 respectively.

Good to know

Low seasonFebruary
Cheapest flight$79
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 28% 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.

  • 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 $258 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 afternoon, which is peak travel time and where the average cost of a ticket is $298.

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 $244 one-way - $221 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 406 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.0Entertainment
7.6Food
Airline reviews

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.

4.0 OkayAidan, Jan 2026
YHM - YEG
Read more Porter Airlines reviews

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

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.

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

Information on your arrival and departure airports