Cheap flights from Toronto to Chicago from C$ 173

In general, June is the cheapest month to fly from Toronto to Chicago Midway Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 110. If you are unable to visit Chicago Midway Airport during the month of June, then departing from Toronto during the month August is also very affordable. Most momondo users find prices during this month for around C$ 112.

The cheapest day to depart on your flight to Chicago Midway Airport is on a Monday when prices can be found for as low as C$ 264. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 320.

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the morning. Flights from Toronto to Chicago Midway Airport during this time can be as low as C$ 290. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the evening when prices are around C$ 665.

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

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

Historically, on average around 16% 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 departing at night 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. Sunday 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.

3 flights are operational daily from Toronto to Chicago Midway Airport as of May 2026. The most popular departure time for this route is 8:00a.m., with 53% of flights per day taking off at noon.

As of May 2026, 26 flights take off from Toronto and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.