£102 Find Cheap Flights from Toronto to Chicago – Compare and Save

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, Monday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Saturday and avoiding Mondays for the best deals.

The cheapest month for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is February, where tickets cost £210 (return) on average. On the other hand, the most expensive months are November and December, where the average cost of round-trip tickets is £259 and £256 respectively.

In the past 5 days, the cheapest return tickets from Toronto to Chicago were found on Air Canada (£166) and United Airlines (£170).

Toronto and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (41 flights per week), American Airlines (35 flights per week), and Air Canada (33 flights per week).

Weekly flights between Toronto and Chicago historically see delays in approximately 13% 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 Saturday 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 9% of their flights encountering any delays.

There are 4 cabin class options for the route. These are First, 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 14 and 16 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 14m. The most common departure time is 18:00 and most flights take off in the morning. Each week, there are 109 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.