Cheap flights from Chicago to Winnipeg from C$ 280

The cheapest month to fly to Winnipeg from Chicago is in February. Flight prices, which tend to average around C$ 88, are often lower during this time because this is during the off-season. If you are unable to visit Winnipeg during the month of February, then departing from Chicago during the month October is also very affordable. Most momondo users find prices during this month for around C$ 115.

In the morning is the cheapest time of day to fly from Chicago to Winnipeg when you can find flight prices for as low as C$ 445. Flying to Winnipeg in the morning is an ideal time because this is during off-peak travel hours. Flights to Winnipeg are more costly in the evening, with an average ticket price of C$ 954. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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

There is only 1 cabin class available to choose from on Chicago to Winnipeg 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 50% on your flight if you consider stops on a Chicago to Winnipeg flight.

As of June 2026, prices for Chicago to Winnipeg flights are approximately 4% more expensive when compared to flights at the same time last year.

As of June 2026, there are 6 flights per day flying from Chicago to Winnipeg. The most common time of day flights depart is 8:00p.m., with 59% of flights taking off in the evening.

As of June 2026, 47 flights take off from Chicago and land in Winnipeg each week. The most common flight departure day for this route is Fri, with 17% of weekly flights taking off on this day.