Cheap flights from Canada to Chicago from C$ 185

In general, February is the cheapest month to fly from Canada to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 432. The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Canada averaging around C$ 437.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 671. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Canada to Chicago O'Hare Intl Airport for around C$ 965.

In the evening is the cheapest time of day to fly from Canada to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 697. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 1,066 on average. Flights to Chicago O'Hare Intl Airport from Canada in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

Fly from Toronto Island to Chicago O'Hare Intl for the best Canada - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 433 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Canada for as low as C$ 243 on momondo.

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

United Airlines, Air Canada, and Delta are the most popular carriers operating from Canada to Chicago O'Hare Intl

Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Canada according to our data. Air Canada is the first choice among our users, with 57% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 6 different airlines that fly to Chicago O'Hare Intl Airport 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 140 minutes.

Generally, flights departing in the morning 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. Saturday 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 9% of their flights experiencing any sort of delay.

As of September 2026, 118 flights take off from Canada and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 1:00p.m., with 47% of daily flights taking off in the afternoon.

As of September 2026, there are 831 flights per week flying from Canada to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.