Cheap flights from Chicago Midway Airport to Canada from $105

If you aren’t able to travel during the month of January, then book flights to Canada from Chicago Midway Airport during April instead. Flights to Canada in April, while not as cheap as those in January, still average around $228.

Our data shows that Saturday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $258. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Canada for around $345.

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Canada when you can find flight prices for as low as $284. Flying to Canada in the morning 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 $290.

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

There are 2 cabin classes available to choose from on Chicago Midway Airport to Canada flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Canada.

Historically, on average around 17% 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 111 minutes.

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

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Tuesday has historically seen more delays on average compared to the rest of the week.

According to our data, Porter Airlines have had the least number of delays on this route over the last 12 months; with about 17% of their flights experiencing any sort of delay.

As of September 2026, there are 4 flights per day flying from Chicago Midway Airport to Canada. The most common time of day flights depart is 11:00AM, with 50% of flights taking off at noon.

The number of flights available between Chicago Midway Airport and Canada is 28 per week as of September 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.