Cheap flights from Toronto to Chicago from $126

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Toronto, with most prices found around $172. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Toronto during the month January is also very affordable. Most momondo users find prices during this month for around $192.

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Toronto. The lowest ticket price found for a Wednesday departure recently was $208. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $294.

Flying to Chicago Midway Airport from Toronto in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $230 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $320. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

There are 2 cabin classes available to choose from on Toronto to Chicago Midway 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 to Chicago Midway Airport.

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 108 minutes.

Generally, flights departing in the evening tend to experience fewer delays. Flights at night 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 14% of their flights experiencing any sort of delay.

As of February 2026, there are 1 flights per day flying from Toronto to Chicago Midway Airport. The most common time of day flights depart is 9:00AM, with 100% of flights taking off at noon.

As of February 2026, there are 8 flights per week flying from Toronto to Chicago Midway Airport. The most common day of the week flights depart is Tue, with 25% of flights taking off on this day.