Cheap flights from Calgary to Chicago from C$ 231

In general, May is the cheapest month to fly from Calgary 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$ 352. The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Calgary averaging around C$ 390.

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$ 627. 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 Calgary to Chicago O'Hare Intl Airport for around C$ 1,106.

In the afternoon is the cheapest time of day to fly from Calgary to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 532. Flying to Chicago O'Hare Intl Airport in the afternoon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 1,008 on average. Flights to Chicago O'Hare Intl Airport from Calgary at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Calgary 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$ 474 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 Calgary for as low as C$ 313 on momondo.

There are 4 cabin classes available to choose from on Calgary 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.

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

WestJet, Air Canada and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Calgary 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 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.

3 flights are operational daily from Calgary to Chicago O'Hare Intl Airport 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.

24 flights are operational weekly from Calgary to Chicago O'Hare Intl Airport as of October 2026. The most popular departure day for this route is Thu, with 42% of flights per week taking off on this day.