Cheap flights from Toronto to Chicago from C$ 211

In general, February is the cheapest month to fly from Toronto 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$ 393. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto averaging around C$ 409.

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$ 686. 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 to Chicago O'Hare Intl Airport for around C$ 939.

In the evening is the cheapest time of day to fly from Toronto to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 705. 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$ 1,124 on average. Flights to Chicago O'Hare Intl Airport from Toronto in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Toronto 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 for as low as C$ 316 on momondo.

There are 4 cabin classes available to choose from on Toronto 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.

You could potentially save up to 6% on your flight if you consider stops on a Toronto to Chicago O'Hare Intl Airport flight.

As of November 2026, prices for Toronto to Chicago O'Hare Intl Airport flights are approximately 2% cheaper when compared to flights at the same time last year.

Porter Airlines, Air Transat, and United Airlines are the most popular carriers operating from Toronto 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 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.

55 flights are operational daily from Toronto to Chicago O'Hare Intl Airport as of November 2026. The most popular departure time for this route is 3:00p.m., with 45% of flights per day taking off in the afternoon.

The number of flights available between Toronto and Chicago O'Hare Intl Airport is 391 per week as of November 2026. The most frequent departure day is Wed, with 17% of weekly flights leaving on this day.