Cheap flights from Chicago to Toronto from C$ 139

The cheapest month to fly to Toronto Island Airport from Chicago is in February. Flight prices, which tend to average around C$ 241, are often lower during this time because this is during the off-season. If you aren’t able to travel to Toronto Island Airport during the month of February, then flying in September is also cheap. Prices for this month can be found on momondo for an average of C$ 303.

On average, the least expensive day to fly to Toronto Island Airport from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as C$ 334. However, this price may fluctuate depending on the airline, the season, and holidays. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 726. These prices are subject to change though, so be sure to set up a Price Alert for flights to Toronto Island Airport.

Flying to Toronto Island Airport from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as C$ 158 when looking at flights departing at noon. In contrast, the most expensive time of day to depart to Toronto Island Airport is in the afternoon when prices are around C$ 443.

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

There is only 1 cabin class available to choose from on Chicago to Toronto Island Airport 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 Island Airport.

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 116 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. 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 16% of their flights experiencing any sort of delay.

As of September 2026, there are 6 flights per day flying from Chicago to Toronto Island Airport. The most common time of day flights depart is 7:00a.m., with 66% of flights taking off at noon.

As of September 2026, 42 flights take off from Chicago and land in Toronto Island Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.