Cheap flights from Chicago Midway Airport to Toronto from C$ 135

The cheapest month to fly to Toronto Island Airport from Chicago Midway Airport is in April. Flight prices, which tend to average around C$ 276, 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 April, then flying in January is also cheap. Prices for this month can be found on momondo for an average of C$ 289.

On average, the least expensive day to fly to Toronto Island Airport from Chicago Midway Airport is on a Thursday. momondo users have found tickets for Thursday departures for as low as C$ 342. 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$ 741. 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 Midway Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as C$ 162 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$ 453.

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

Historically, on average around 17% 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.

Saturday 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 17% of their flights experiencing any sort of delay.

2 flights are operational daily from Chicago Midway Airport to Toronto Island Airport as of September 2026. The most popular departure time for this route is 11:00a.m., with 50% of flights per day taking off at noon.

As of September 2026, 16 flights take off from Chicago Midway Airport and land in Toronto Island Airport each week. The most common flight departure day for this route is Wed, with 25% of weekly flights taking off on this day.