Cheap flights from Chicago to Toronto from $87

If you aren’t able to travel during the month of February, then book flights to Toronto Island Airport from Chicago during September instead. Flights to Toronto Island Airport in September, while not as cheap as those in February, still average around $238.

The cheapest day to depart on your flight to Toronto Island Airport is on a Saturday when prices can be found for as low as $269. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $339. These prices are subject to change though, so be sure to set up a Price Alert for flights to Toronto Island Airport.

Our data shows that the cheapest Chicago to Toronto Island Airport flights are usually those with departure times in the morning. Our users have found flights to Toronto Island Airport in the morning for as low as $290. In contrast, the most expensive time of day to depart to Toronto Island Airport is at noon when prices are around $339.

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

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

Historically, on average around 22% 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 117 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. Friday 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 17% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Toronto Island Airport is 8 per day as of September 2026. The most frequent departure time is 7:00AM, with 50% of daily flights leaving at noon.

56 flights are operational weekly from Chicago to Toronto Island Airport as of September 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.