Cheap flights from Canada to Chicago from C$ 181

In general, January is the cheapest month to fly from Canada to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 288. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Canada during the month February is also very affordable. Most momondo users find prices during this month for around C$ 298.

The cheapest day to depart on your flight to Chicago Midway Airport is on a Thursday when prices can be found for as low as C$ 331. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 374.

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is at noon. Flights from Canada to Chicago Midway Airport during this time can be as low as C$ 339. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 684.

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

Historically, on average around 16% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 107 minutes.

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

Thursday 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 September 2026, there are 4 flights per day flying from Canada to Chicago Midway Airport. The most common time of day flights depart is 10:00a.m., with 50% of flights taking off at noon.

As of September 2026, 28 flights take off from Canada and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.