Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 191

In general, January is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 386. The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 394.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 684. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport for around C$ 956.

In the evening is the cheapest time of day to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 702. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 1,117 on average. Flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 442 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport for as low as C$ 317 on momondo.

There are 4 cabin classes available to choose from on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

United Airlines is the most popular carrier operating from Toronto Pearson Intl to Chicago O'Hare Intl

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport according to our data. Air Canada is the first choice among our users, with 64% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport 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. Saturday 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 9% of their flights experiencing any sort of delay.

As of October 2026, there are 36 flights per day flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. The most common time of day flights depart is 1:00p.m., with 43% of flights taking off in the afternoon.

The number of flights available between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport is 257 per week as of October 2026. The most frequent departure day is Wed, with 26% of weekly flights leaving on this day.