Cheap flights from Chicago to Canada from $61

If you aren’t able to travel during the month of September, then book flights to Canada from Chicago during July instead. Flights to Canada in July, while not as cheap as those in September, still average around $235.

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 $503. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Canada for around $750.

In the evening is the cheapest time of day to fly from Chicago to Canada when you can find flight prices for as low as $428. Flying to Canada in the evening is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Canada is in the afternoon when prices are around $743.

Fly from Chicago O'Hare Intl to Calgary 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 $287 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 $152 on momondo.

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

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

United Airlines, Air Canada and American Airlines 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 30% of people opting to fly with this airline when traveling to Canada. Keep in mind that there are 7 different airlines that fly to Canada on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% 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 in the evening 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. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Korean Air have had the least number of delays on this route over the last 12 months; with about 11% of their flights experiencing any sort of delay.

As of February 2026, there are 89 flights per day flying from Chicago to Canada. The most common time of day flights depart is 6:00PM, with 41% of flights taking off in the afternoon.

The number of flights available between Chicago and Canada is 628 per week as of February 2026. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.