Cheap flights from Toronto Pearson Intl Airport to Chicago from $122

The month of September is, on average, the cheapest month to fly to Chicago from Toronto Pearson Intl Airport, with most prices found around $231. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Toronto Pearson Intl Airport to Chicago during January average around $236.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $420. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Pearson Intl Airport to Chicago for around $691.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Toronto Pearson Intl Airport to Chicago during this time can be as low as $381. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $627.

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 $286 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 $195 on momondo.

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

As of March 2026, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 5% 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 47% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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 141 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Monday 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, United Airlines have had the least number of delays on this route over the last 12 months; with about 8% of their flights experiencing any sort of delay.

The number of flights available between Toronto Pearson Intl Airport and Chicago is 58 per day as of March 2026. The most frequent departure time is 6:00AM, with 46% of daily flights leaving at noon.

The number of flights available between Toronto Pearson Intl Airport and Chicago is 406 per week as of March 2026. The most frequent departure day is Sun, with 16% of weekly flights leaving on this day.