Cheap flights from Canada to Chicago from C$ 192

The month of November is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 388.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 649. 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 Sunday because tickets tend to average around C$ 1,073. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the morning is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 719. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,070 per ticket.

Fly from Winnipeg to Chicago O'Hare Intl 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 C$ 432 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 C$ 249 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.

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

Air Canada, United Airlines and WestJet 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 50% of people opting to fly with this airline when travelling 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 departing in the evening have, in the past, seen delays more frequently in comparison.

Thursday 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, United Airlines has had the least 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 126 per day as of June 2026. The most frequent departure time is 1:00p.m., with 45% of daily flights leaving in the afternoon.

882 flights are operational weekly from Canada to Chicago as of June 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.