Cheap flights from Canada to Chicago from $111

The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Canada averaging around $244.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $459. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Canada because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $735.

Flying to Chicago O'Hare Intl Airport from Canada in the evening is the least expensive time of day to depart. momondo users have found prices as low as $371 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $692. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Montreal Pierre Elliott Trudeau Intl 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 $285 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 $195 on momondo.

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

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

Air Canada, United Airlines and American Airlines 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 45% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 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 142 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.

Monday 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 8% of their flights experiencing any sort of delay.

As of March 2026, 106 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 6:00AM, with 53% of daily flights taking off in the afternoon.

As of March 2026, there are 742 flights per week flying from Canada to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Fri, with 15% of flights taking off on this day.