Cheap flights from Chicago O'Hare Intl Airport to Calgary from $61

The month of May is, on average, the cheapest month to fly to Calgary from Chicago O'Hare Intl Airport, with most prices found around $199. If you aren’t able to travel during the month of May, then book flights to Calgary from Chicago O'Hare Intl Airport during October instead. Flights to Calgary in October, while not as cheap as those in May, still average around $221.

The cheapest day to depart on your flight to Calgary is on a Monday when prices can be found for as low as $288. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago O'Hare Intl Airport to Calgary on a Saturday will generally be more expensive and average around $333. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

The cheapest time of day to fly to Calgary is at noon when flights can be purchased for as low as $255. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $444 on average. Flights to Calgary from Chicago O'Hare Intl Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

You are more likely to see cheaper flights to Calgary from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Calgary for around $278 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Calgary from Chicago O'Hare Intl Airport for as low as $242 on momondo.

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

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

WestJet, American Airlines and United Airlines are the top three most popular airlines that fly to Calgary from Chicago O'Hare Intl Airport according to our data. WestJet is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Calgary. Keep in mind that there are 5 different airlines that fly to Calgary on a routine basis, so you have a few additional options to choose from.

Historically, on average around 29% of flights between Chicago and Calgary have experienced a delay on any given week. The average delay length over the past 12 months has been 143 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 25% of their flights experiencing any sort of delay.

2 flights are operational daily from Chicago O'Hare Intl Airport to Calgary as of February 2026. The most popular departure time for this route is 8:00AM, with 91% of flights per day taking off at noon.

18 flights are operational weekly from Chicago O'Hare Intl Airport to Calgary as of February 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.