Cheap flights from Toronto Pearson Intl Airport to Chicago from $139

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto Pearson Intl Airport averaging around $283.

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 $481. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto Pearson Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $669.

Flying to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $427 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $789. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 $314 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 $226 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.

Delta and United Airlines are the most popular carriers 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 52% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 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 in the evening have, in the past, seen delays more frequently in comparison.

Thursday is statistically the day of the week which experiences the fewest number of 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 have had the least number of 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 33 flights per day flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. The most common time of day flights depart is 3:00PM, with 46% of flights taking off in the afternoon.

231 flights are operational weekly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport as of October 2026. The most popular departure day for this route is Thu, with 28% of flights per week taking off on this day.