Cheap flights from Chicago to Toronto from C$ 139

If you aren’t able to travel during the month of February, then book flights to Toronto Pearson Intl Airport from Chicago during June instead. Flights to Toronto Pearson Intl Airport in June, while not as cheap as those in February, still average around C$ 94.

Our data shows that Thursday is the least expensive day to fly to Toronto Pearson Intl Airport. Tickets to fly out on this day can be as low as C$ 258. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Toronto Pearson Intl Airport for around C$ 504.

Our data shows that the cheapest Chicago to Toronto Pearson Intl Airport flights are usually those with departure times in the evening. Our users have found flights to Toronto Pearson Intl Airport in the evening for as low as C$ 254. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 445 on average. Flights to Toronto Pearson Intl Airport from Chicago in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You are more likely to see cheaper flights to Toronto Pearson Intl Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Toronto Pearson Intl Airport for around C$ 417 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Toronto Pearson Intl Airport from Chicago for as low as C$ 278 on momondo.

You could potentially save up to 9% on your flight if you consider stops on a Chicago to Toronto Pearson Intl Airport flight.

As of May 2026, prices for Chicago to Toronto Pearson Intl Airport flights are approximately 16% cheaper when compared to flights at the same time last year.

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

United Airlines, Air Canada and American Airlines are the top three most popular airlines that fly to Toronto Pearson Intl Airport from Chicago according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when travelling to Toronto Pearson Intl Airport. Keep in mind that there are 3 different airlines that fly to Toronto Pearson Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between Chicago and Toronto have experienced a delay on any given week. The average delay length over the past 12 months has been 132 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.

Tuesday 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 17% of their flights experiencing any sort of delay.

As of May 2026, there are 60 flights per day flying from Chicago to Toronto Pearson Intl Airport. The most common time of day flights depart is 8:00p.m., with 40% of flights taking off at noon.

As of May 2026, 424 flights take off from Chicago and land in Toronto Pearson Intl Airport each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.