Cheap flights from Toronto to Chicago from $153

The month of January is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around $248. If you’re not able to fly to Chicago in January, then March is your next best option. Flight prices from Toronto to Chicago during March average around $271.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $449. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto to Chicago for around $671.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Toronto to Chicago during this time can be as low as $407. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $814.

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

You are more likely to see cheaper flights to Chicago from Toronto when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $313 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as $226 on momondo.

There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 2% on your flight if you consider stops on a Toronto to Chicago flight.

As of September 2026, prices for Toronto to Chicago flights are approximately 13% cheaper when compared to flights at the same time last year.

Porter Airlines, Air Canada, and United Airlines are the most popular carriers operating from Toronto to Chicago

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Toronto according to our data. Air Canada is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 14% 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 134 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening 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. Saturday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 9% of their flights experiencing any sort of delay.

The number of flights available between Toronto and Chicago is 72 per day as of September 2026. The most frequent departure time is 1:00PM, with 46% of daily flights leaving in the afternoon.

As of September 2026, 509 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Sun, with 16% of weekly flights taking off on this day.