Cheap flights from Alberta to Chicago from C$ 230

The month of May is another great option to travel to Chicago, with average flight prices from Alberta averaging around C$ 381.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 626. 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$ 1,104. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the afternoon is the cheapest time of day to fly from Alberta to Chicago when you can find flight prices for as low as C$ 531. Flying to Chicago in the afternoon 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$ 1,007 per ticket.

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

You are more likely to see cheaper flights to Chicago from Alberta when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 473 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Alberta for as low as C$ 313 on momondo.

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

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

WestJet, Air Canada and United Airlines are the top three most popular airlines that fly to Chicago from Alberta according to our data. WestJet is the first choice among our users, with 42% 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.

3 flights are operational daily from Alberta to Chicago as of October 2026. The most popular departure time for this route is 1:00p.m., with 100% of flights per day taking off in the afternoon.

The number of flights available between Alberta and Chicago is 24 per week as of October 2026. The most frequent departure day is Thu, with 42% of weekly flights leaving on this day.