Cheap flights from Chicago to Toronto from C$ 139

The month of February is, on average, the cheapest month to fly to Toronto from Chicago, with most prices found around C$ 385. The month of June is another great option to travel to Toronto, with average flight prices from Chicago averaging around C$ 415.

According to our data, Tuesday is the cheapest day to fly to Toronto from Chicago. The lowest ticket price found for a Tuesday departure recently was C$ 364. 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 Saturday will generally be more expensive and average around C$ 491. 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$ 353 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around C$ 483. 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$ 465 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$ 375 on momondo.

There are 3 cabin classes available to choose from on Chicago to Toronto flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of September 2026, prices for Chicago to Toronto flights are approximately 38% cheaper when compared to flights at the same time last year.

Porter Airlines, American Airlines, and United Airlines 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 48% 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 21% 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 15% of their flights experiencing any sort of delay.

As of September 2026, there are 45 flights per day flying from Chicago to Toronto. The most common time of day flights depart is 8:00p.m., with 43% of flights taking off at noon.

As of September 2026, 320 flights take off from Chicago and land in Toronto each week. The most common flight departure day for this route is Tue, with 24% of weekly flights taking off on this day.