Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 248

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$ 330. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto Pearson Intl Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 391.

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is at noon. Flights from Toronto Pearson Intl Airport to Chicago Midway Airport during this time can be as low as C$ 340. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 689.

Historically, on average around 29% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 108 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.

Wednesday 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, Delta has had the least delays on this route over the last 12 months, with about 49% of their flights experiencing any sort of delay.