Cheap flights from Toronto Island Airport to Chicago from C$ 182

The month of December is another great option to travel to Chicago, with average flight prices from Toronto Island Airport averaging around C$ 309.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 628. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 937. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the evening is the cheapest time of day to fly from Toronto Island Airport to Chicago when you can find flight prices for as low as C$ 699. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,083 per ticket.

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

There are 3 cabin classes available to choose from on Toronto Island Airport to Chicago 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 Toronto Island Airport to Chicago.

Historically, on average around 15% 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 107 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon 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. Monday 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.

8 flights are operational daily from Toronto Island Airport to Chicago as of September 2026. The most popular departure time for this route is 10:00a.m., with 50% of flights per day taking off in the afternoon.

As of September 2026, 56 flights take off from Toronto Island Airport and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.