Cheap flights from Chicago to Calgary from R2 579

The month of May is another great option to travel to Calgary, with average flight prices from Chicago averaging around R5 027.

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 R5 878 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Calgary from Chicago for as low as R5 241 on momondo.

There is only 1 cabin class 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.

Historically, on average around 26% 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 144 minutes.

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

Tuesday 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 have had the fewest delays on this route over the last 12 months, with about 24% of their flights experiencing any sort of delay.

As of October 2026, there are 4 flights per day flying from Chicago to Calgary. The most common time of day flights depart is 8:00, with 93% of flights taking off at midday.

32 flights are operational weekly from Chicago to Calgary as of October 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.