$66 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 2/26. 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$185
Calgary
Calgary1 stop$226
Halifax
Halifax2 stops$256
Ottawa
Ottawa1 stop$274
Québec City
Québec City1 stop$486
Winnipeg
Winnipeg1 stop$221
St. John's
St. John's2 stops$488
Saskatoon
Saskatoon1 stop$1,013
Thunder Bay
Thunder Bay2 stops$355
Toronto
Torontononstop$185
Calgary
Calgary1 stop$226
Halifax
Halifax2 stops$256
Ottawa
Ottawa1 stop$274
Québec City
Québec City1 stop$486
Winnipeg
Winnipeg1 stop$221
St. John's
St. John's2 stops$488
Saskatoon
Saskatoon1 stop$1,013
Thunder Bay
Thunder Bay2 stops$355

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

Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
Multiple Airlines Logo
2:30 pm - 3:20 pm
YTZ
-
MDW
1h 50mnonstop
$185Multiple Airlines
Thu, Jan 22 - Mon, Jan 26
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
$190Porter Airlines
Mon, Jan 19 - Mon, Jan 26
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
$192Porter Airlines
Tue, Jan 20 - Tue, Jan 27
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
$193Porter Airlines
Mon, Jan 19 - Mon, Jan 26
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
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
5:01 pm - 3:07 pm
MDW
-
YWG
22h 06m1 stop
Multiple Airlines Logo
7:30 am - 10:19 pm
YWG
-
MDW
14h 49m1 stop
$221Multiple Airlines
Sat, Feb 14 - Wed, Feb 18
Delta Logo
9:34 am - 4:10 pm
MDW
-
YYZ
5h 36m1 stop
Delta Logo
6:15 am - 8:53 am
YYZ
-
MDW
3h 38m1 stop
$233Delta
Thu, Jan 29 - Sun, Feb 1
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
$234Delta
Thu, Jan 29 - Sun, Feb 1
WestJet Logo
1:26 pm - 12:42 am
MDW
-
YWG
11h 16m2 stops
WestJet Logo
5:00 am - 5:55 pm
YWG
-
MDW
12h 55m2 stops
$474WestJet
Thu, Jan 29 - Sun, Feb 1
WestJet Logo
10:48 am - 3:07 pm
MDW
-
YWG
28h 19m1 stop
WestJet Logo
5:00 am - 5:55 pm
YWG
-
MDW
12h 55m2 stops
$480WestJet
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 $171 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 $171.

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 $272, 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 March and June, when the average cost of round-trip tickets is $375 and $371 respectively.

Good to know

Low seasonJanuary
Cheapest flight$66
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly and prices are also 29% lower on average.
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.

  • 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 $262 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 at night, which is peak travel time and where the average cost of a ticket is $360.

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 $122 one-way - $262 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 397 reviews
8.0Comfort
8.6Crew
7.6Food
8.2Boarding
7.0Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Dec 2025
LGA - YYZ
Read more Porter Airlines reviews

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.

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!

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

Information on your arrival and departure airports