Cheap flights from Chicago to Toronto from $106

The cheapest month to fly to Toronto Pearson Intl Airport from Chicago is in February. Flight prices, which tend to average around $288, are often lower during this time because this is during the off-season. If you don’t want to visit Toronto Pearson Intl Airport in February, then you should wait until November to fly from Chicago, when ticket prices are also cheap, with an average price of $295.

The cheapest day to depart from Chicago to Toronto Pearson Intl Airport is on a Thursday when prices can be found for as low as $437. The most expensive day to fly to Toronto Pearson Intl Airport is Monday, with ticket prices averaging around $678.

Flying to Toronto Pearson Intl Airport from Chicago in the evening is the least expensive time of day to depart. momondo users have found prices as low as $438 when looking at flights departing in the evening. Flights in the afternoon are often more expensive with an average ticket price of $787.

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 $330 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 $285 on momondo.

There are 4 cabin classes available to choose from on Chicago to Toronto Pearson Intl Airport 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 to Toronto Pearson Intl Airport.

As of August 2026, prices for Chicago to Toronto Pearson Intl Airport flights are approximately 15% more expensive when compared to flights at the same time last year.

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 40% of people opting to fly with this airline when traveling to Toronto Pearson Intl Airport. Keep in mind that there are 7 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 22% 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 in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Toronto Pearson Intl Airport is 47 per day as of August 2026. The most frequent departure time is 8:00PM, with 40% of daily flights leaving at noon.

334 flights are operational weekly from Chicago to Toronto Pearson Intl Airport as of August 2026. The most popular departure day for this route is Fri, with 21% of flights per week taking off on this day.