Cheap flights from Chicago to Canada from C$ 135

In general, October is the cheapest month to fly from Chicago to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 326. If you’re not able to fly to Canada in October, then November is your next best option. Flight prices from Chicago to Canada during November average around C$ 390.

Our data shows that Thursday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 260. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 488. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

According to our data, the cheapest time of day to fly to Canada is in the evening. momondo users have found flights departing from Chicago to Canada in the evening for as low as C$ 256. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 461 per ticket.

Fly from Chicago Midway to Toronto Island for the best Chicago - Canada flight prices

You are more likely to see cheaper flights to Canada from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Canada for around C$ 421 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Canada from Chicago for as low as C$ 279 on momondo.

Porter Airlines, United Airlines, and Delta are the most popular carriers operating from Chicago to Canada

United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Canada from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when travelling to Canada. Keep in mind that there are 4 different airlines that fly to Canada on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between Chicago and Canada have experienced a delay on any given week. The average delay length over the past 12 months has been 136 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.

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 has had the least delays on this route over the last 12 months, with about 18% of their flights experiencing any sort of delay.

85 flights are operational daily from Chicago to Canada as of May 2026. The most popular departure time for this route is 8:00a.m., with 46% of flights per day taking off at noon.

As of May 2026, 599 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.