Cheap flights from Chicago to Toronto from $109

The month of February is, on average, the cheapest month to fly to Toronto from Chicago, with most prices found around $286. If you are unable to visit Toronto during the month of February, then departing from Chicago during the month June is also very affordable. Most momondo users find prices during this month for around $302.

On average, the least expensive day to fly to Toronto from Chicago is on a Thursday. momondo users have found tickets for Thursday departures for as low as $397. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Toronto is Monday, with ticket prices averaging around $578.

In the morning is the cheapest time of day to fly from Chicago to Toronto when you can find flight prices for as low as $404. Flying to Toronto in the morning is an ideal time because this is during off-peak travel hours. Flights to Toronto are more costly in the afternoon, with an average ticket price of $716. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

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

You are more likely to see cheaper flights to Toronto from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Toronto for around $335 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Toronto from Chicago for as low as $272 on momondo.

There are 4 cabin classes available to choose from on Chicago to Toronto 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.

As of October 2026, prices for Chicago to Toronto flights are approximately 36% 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 Chicago to Toronto

United Airlines, Air Canada and American Airlines are the top three most popular airlines that fly to Toronto from Chicago according to our data. United Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Toronto. Keep in mind that there are 6 different airlines that fly to Toronto on a routine basis, so you have a few additional options to choose from.

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 133 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.

Tuesday 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, American 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 is 54 per day as of October 2026. The most frequent departure time is 2:00PM, with 42% of daily flights leaving in the afternoon.

381 flights are operational weekly from Chicago to Toronto as of October 2026. The most popular departure day for this route is Sun, with 19% of flights per week taking off on this day.