Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 187

The month of September is another great option to travel to Chicago, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 92.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 609. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,043. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the morning is the cheapest time of day to fly from Toronto Pearson Intl Airport to Chicago when you can find flight prices for as low as C$ 689. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,099 per ticket.

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Toronto Pearson Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 410 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto Pearson Intl Airport for as low as C$ 252 on momondo.

You could potentially save up to 6% on your flight if you consider stops on a Toronto Pearson Intl Airport to Chicago flight.

As of May 2026, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 1% cheaper when compared to flights at the same time last year.

United Airlines and Delta are the most popular carriers operating from Toronto Pearson Intl to Chicago

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Toronto Pearson Intl Airport according to our data. Air Canada is the first choice among our users, with 54% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 13% 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 139 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the evening 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. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 8% of their flights experiencing any sort of delay.

54 flights are operational daily from Toronto Pearson Intl Airport to Chicago as of May 2026. The most popular departure time for this route is 1:00p.m., with 44% of flights per day taking off in the afternoon.

The number of flights available between Toronto Pearson Intl Airport and Chicago is 380 per week as of May 2026. The most frequent departure day is Fri, with 18% of weekly flights leaving on this day.