Cheap flights from Winnipeg to Calgary from C$ 110

The cheapest month to fly to Calgary from Winnipeg is in September. Flight prices, which tend to average around C$ 147, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Calgary from Winnipeg during October instead. Flights to Calgary in October, while not as cheap as those in September, still average around C$ 172.

The cheapest day to depart on your flight to Calgary is on a Friday when prices can be found for as low as C$ 312. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 393.

Our data shows that the cheapest Winnipeg to Calgary flights are usually those with departure times in the evening. Our users have found flights to Calgary in the evening for as low as C$ 283. If you have a flexible travel schedule, then try to avoid flying at noon when prices are C$ 543 on average. Flights to Calgary from Winnipeg at noon are generally more expensive because this time of day is more convenient for travellers’ schedules.

Fly from Winnipeg to Calgary for the best Winnipeg - Calgary flight prices

You are more likely to see cheaper flights to Calgary from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Calgary for around C$ 252 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Calgary from Winnipeg for as low as C$ 183 on momondo.

There are 3 cabin classes available to choose from on Winnipeg to Calgary flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

WestJet is the most popular carrier operating from Winnipeg to Calgary

WestJet, Flair Airlines and Air Canada are the top three most popular airlines that fly to Calgary from Winnipeg according to our data. WestJet is the first choice among our users, with 74% of people opting to fly with this airline when travelling to Calgary. Keep in mind that there are 3 different airlines that fly to Calgary on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% of flights between Winnipeg and Calgary have experienced a delay on any given week. The average delay length over the past 12 months has been 118 minutes.

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

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

According to our data, Air Canada has had the least delays on this route over the last 12 months, with about 13% of their flights experiencing any sort of delay.

As of April 2026, 12 flights take off from Winnipeg and land in Calgary each day. The most common flight departure time for this route is 6:00a.m., with 59% of daily flights taking off at noon.

As of April 2026, there are 90 flights per week flying from Winnipeg to Calgary. The most common day of the week flights depart is Mon, with 23% of flights taking off on this day.