Cheap flights from Chicago Midway Airport to Canada from C$ 149

In general, January is the cheapest month to fly from Chicago Midway Airport to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 287. If you’re not able to fly to Canada in January, then April is your next best option. Flight prices from Chicago Midway Airport to Canada during April average around C$ 319.

Our data shows that Wednesday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 314. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 737. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

According to our data, the cheapest time of day to fly to Canada is in the morning. momondo users have found flights departing from Chicago Midway Airport to Canada in the morning for as low as C$ 399. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 467 per ticket.

Fly from Chicago Midway to Toronto Island for the best Chicago Midway - Canada flight prices

There is only 1 cabin class available to choose from on Chicago Midway Airport to Canada flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Canada.

Historically, on average around 16% of flights between Chicago and Canada have experienced a delay on any given week. The average delay length over the past 12 months has been 114 minutes.

Generally, flights departing in the evening tend to experience fewer delays. Flights departing at night have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Porter Airlines has had the least delays on this route over the last 12 months, with about 15% of their flights experiencing any sort of delay.

As of August 2026, there are 2 flights per day flying from Chicago Midway Airport to Canada. The most common time of day flights depart is 10:00a.m., with 53% of flights taking off at noon.

14 flights are operational weekly from Chicago Midway Airport to Canada as of August 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.