Cheap flights from Chicago to Toronto from C$ 133

The month of November is, on average, the cheapest month to fly to Toronto from Chicago, with most prices found around C$ 79. The month of March is another great option to travel to Toronto, with average flight prices from Chicago averaging around C$ 79.

According to our data, Thursday is the cheapest day to fly to Toronto from Chicago. The lowest ticket price found for a Thursday departure recently was C$ 306. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. Flights from Chicago to Toronto on a Monday will generally be more expensive and average around C$ 486. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Flying to Toronto from Chicago in the evening is the least expensive time of day to depart. momondo users have found prices as low as C$ 259 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around C$ 402. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago Midway to Toronto Island for the best Chicago - Toronto flight prices

You are more likely to see cheaper flights to Toronto from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Toronto for around C$ 417 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Toronto from Chicago for as low as C$ 277 on momondo.

No. A direct flight is the cheapest option for a flight between Chicago to Toronto.

As of May 2026, prices for Chicago to Toronto flights are approximately 25% cheaper when compared to flights at the same time last year.

Porter Airlines, Delta, and Air Canada are the most popular carriers operating from Chicago to Toronto

United Airlines, Air Canada and American Airlines are the top three most popular airlines that fly to Toronto from Chicago according to our data. United Airlines is the first choice among our users, with 54% of people opting to fly with this airline when travelling to Toronto. Keep in mind that there are 3 different airlines that fly to Toronto on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% of flights between Chicago and Toronto have experienced a delay on any given week. The average delay length over the past 12 months has been 131 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.

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, Porter Airlines has had the least delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

As of May 2026, there are 64 flights per day flying from Chicago to Toronto. The most common time of day flights depart is 2:00p.m., with 44% of flights taking off at noon.

As of May 2026, 454 flights take off from Chicago and land in Toronto each week. The most common flight departure day for this route is Fri, with 16% of weekly flights taking off on this day.