Cheap flights from Canada to Chicago from $133

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Canada, with most prices found around $204. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Canada during the month September is also very affordable. Most momondo users find prices during this month for around $207.

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Canada. The lowest ticket price found for a Tuesday departure recently was $229. 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, Friday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $337.

Flying to Chicago Midway Airport from Canada in the morning is the least expensive time of day to depart. momondo users have found prices as low as $283 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $347. 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 Canada - Chicago Midway flight prices

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

Historically, on average around 16% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 106 minutes.

Generally, flights departing in the morning 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 15% of their flights experiencing any sort of delay.

As of August 2026, 3 flights take off from Canada and land in Chicago Midway Airport each day. The most common flight departure time for this route is 1:00PM, with 66% of daily flights taking off in the afternoon.

As of August 2026, there are 22 flights per week flying from Canada to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.