Cheap flights from Chicago to Calgary from C$ 153

The cheapest month to fly to Calgary from Chicago is in November. Flight prices, which tend to average around C$ 83, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Calgary from Chicago during October instead. Flights to Calgary in October, while not as cheap as those in November, still average around C$ 84.

The cheapest day to depart on your flight to Calgary is on a Sunday when prices can be found for as low as C$ 264. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 593.

Our data shows that the cheapest Chicago to Calgary flights are usually those with departure times at noon. Our users have found flights to Calgary at noon for as low as C$ 254. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 403 on average. Flights to Calgary from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You are more likely to see cheaper flights to Calgary from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Calgary for around C$ 429 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Calgary from Chicago for as low as C$ 375 on momondo.

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

You could potentially save up to 16% on your flight if you consider stops on a Chicago to Calgary flight.

As of May 2026, prices for Chicago to Calgary flights are approximately 24% cheaper when compared to flights at the same time last year.

Historically, on average around 31% 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 142 minutes.

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

Thursday is statistically the day of the week that experiences the fewest delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 27% of their flights experiencing any sort of delay.

As of May 2026, there are 10 flights per day flying from Chicago to Calgary. The most common time of day flights depart is 8:00p.m., with 64% of flights taking off in the evening.

As of May 2026, 74 flights take off from Chicago and land in Calgary each week. The most common flight departure day for this route is Wed, with 16% of weekly flights taking off on this day.