Cheap flights from Chicago to Canada from $104

If you aren’t able to travel during the month of February, then book flights to Canada from Chicago during May instead. Flights to Canada in May, while not as cheap as those in February, still average around $343.

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 $415. 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 $636.

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 $420. 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 $791.

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 $335 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 $272 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.

Air Canada, Porter 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 36% of people opting to fly with this airline when traveling to Canada. Keep in mind that there are 9 different airlines that fly to Canada on a routine basis, so you have a few additional options to choose from.

Historically, on average around 22% 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 138 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. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

As of October 2026, there are 115 flights per day flying from Chicago to Canada. The most common time of day flights depart is 10:00AM, with 41% of flights taking off at noon.

The number of flights available between Chicago and Canada is 805 per week as of October 2026. The most frequent departure day is Tue, with 16% of weekly flights leaving on this day.