Cheap flights from Chicago O'Hare Intl Airport to Calgary from $143

The month of January is, on average, the cheapest month to fly to Calgary from Chicago O'Hare Intl Airport, with most prices found around $243. If you aren’t able to travel during the month of January, then book flights to Calgary from Chicago O'Hare Intl Airport during May instead. Flights to Calgary in May, while not as cheap as those in January, still average around $307.

The cheapest day to depart on your flight to Calgary is on a Friday when prices can be found for as low as $371. 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 Thursday will generally be more expensive and average around $423. 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 $287. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $509 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 $366 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 $317 on momondo.

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

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

WestJet, United Airlines and American 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 41% of people opting to fly with this airline when traveling to Calgary. Keep in mind that there are 6 different airlines that fly to Calgary on a routine basis, so you have a few additional options to choose from.

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 at night have, in the past, seen delays more frequently in comparison.

Tuesday 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 24% of their flights experiencing any sort of delay.

Toronto (YYZ) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

Flights via Minneapolis (MSP) offer the lowest average round-trip price of $251.

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 6h 01m.

Minneapolis (MSP) has the shortest average layover time for this route: 1h 27m.

1 flights are operational daily from Chicago O'Hare Intl Airport to Calgary as of November 2026. The most popular departure time for this route is 8:00AM, with 100% of flights per day taking off at noon.

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