Cheap flights from Canada to Chicago from $135

The month of April is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $255. If you’re not able to fly to Chicago in April, then November is your next best option. Flight prices from Canada to Chicago during November average around $273.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $437. 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 Canada to Chicago for around $697.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Canada to Chicago during this time can be as low as $383. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $695.

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

You are more likely to see cheaper flights to Chicago from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $304 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as $175 on momondo.

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

United Airlines, Air Transat, and Delta are the most popular carriers operating from Canada to Chicago

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Canada according to our data. Air Canada is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 13% 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 136 minutes.

Generally, flights departing at night 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. Sunday 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 8% of their flights experiencing any sort of delay.

The number of flights available between Canada and Chicago is 115 per day as of June 2026. The most frequent departure time is 1:00PM, with 45% of daily flights leaving in the afternoon.

As of June 2026, there are 808 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Tue, with 17% of flights taking off on this day.