Cheap flights from Chicago to Calgary from $107

The month of November is, on average, the cheapest month to fly to Calgary from Chicago, with most prices found around $60. 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 $61.

The cheapest day to depart on your flight to Calgary is on a Friday when prices can be found for as low as $310. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago to Calgary on a Saturday will generally be more expensive and average around $347. 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 in the afternoon when flights can be purchased for as low as $279. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $453 on average. Flights to Calgary from Chicago 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 - 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 $301 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 $244 on momondo.

No. A direct flight is the cheapest option for a flight between Chicago to Calgary.

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

United Airlines, Delta, and WestJet are the most popular carriers operating from Chicago to Calgary

WestJet, American Airlines and United Airlines are the top three most popular airlines that fly to Calgary from Chicago according to our data. WestJet is the first choice among our users, with 44% 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 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 140 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.

Thursday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 27% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Calgary is 3 per day as of May 2026. The most frequent departure time is 8:00AM, with 83% of daily flights leaving at noon.

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