£101 Find Cheap Flights from Toronto to Chicago

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Thursday and avoiding Saturdays for the best deals.

The cheapest month for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is January, where tickets cost £190 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is £247 and £242 respectively.

In the past 3 days, the cheapest return tickets from Toronto to Chicago were found on United Airlines (£154) and Air Canada (£157).

United Airlines connects Toronto to Chicago with 53 flights per week. American Airlines also offers 35 flights per week, while Air Canada follows with 35 flights per week.

Weekly flights between Toronto and Chicago historically see delays in approximately 12% of cases, with the average delay over the past year being 139 minutes.

Typically, flights leaving in the morning tend to face fewer delays, whereas flights in the evening have historically encountered delays more often.

Statistically, Thursday is the day of the week with the fewest delays on this flight route, while Sunday has typically experienced more delays than other days.

Based on our data, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 8% of their flights encountering any delays.

There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are between 15 and 18 direct flights that take off from Toronto Pearson Intl Airport and land in Chicago O'Hare Intl Airport, with an average flight time of 2h 01m. The most common departure time is 17:00 and most flights take off in the morning. Each week, there are 123 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.