Cheap flights from Toronto Island Airport to Chicago from $134

The month of September is, on average, the cheapest month to fly to Chicago from Toronto Island Airport, with most prices found around $195. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Toronto Island Airport to Chicago during January average around $223.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $450. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Island Airport to Chicago for around $684.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Toronto Island Airport to Chicago during this time can be as low as $388. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $743.

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

There are 4 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 110 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Porter Airlines have had the least number of delays on this route over the last 12 months; with about 15% of their flights experiencing any sort of delay.

The number of flights available between Toronto Island Airport and Chicago is 6 per day as of August 2026. The most frequent departure time is 12:00PM, with 57% of daily flights leaving in the afternoon.

As of August 2026, there are 44 flights per week flying from Toronto Island Airport to Chicago. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.