Cheap flights from Calgary to Chicago from C$ 183

The month of September is another great option to travel to Chicago, with average flight prices from Calgary averaging around C$ 87.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 604. 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$ 1,085. 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 Calgary to Chicago when you can find flight prices for as low as C$ 699. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,333 per ticket.

Fly from Calgary to Chicago O'Hare Intl for the best Calgary - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 384 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Calgary for as low as C$ 296 on momondo.

United Airlines and Delta are the most popular carriers operating from Calgary to Chicago

WestJet, American Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Calgary according to our data. WestJet is the first choice among our users, with 48% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Toronto (YYZ) was the most common stop: 43% of momondo users choosing one-stop flights on this route connected there.

Flights via Denver (DEN) offer the lowest average round-trip price of C$ 262.

Flights connecting via Denver (DEN) have the shortest average one-way travel time: 7h 35m.

Toronto (YYZ) has the shortest average layover time for this route: 2h 17m.

As of April 2026, there are 7 flights per day flying from Calgary to Chicago. The most common time of day flights depart is 12:00p.m., with 94% of flights taking off in the afternoon.

55 flights are operational weekly from Calgary to Chicago as of April 2026. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.