Cheap flights from Chicago to Montreal from C$ 96

The cheapest month to fly to Montreal from Chicago is in April. Flight prices, which tend to average around C$ 390, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of April, then book flights to Montreal from Chicago during September instead. Flights to Montreal in September, while not as cheap as those in April, still average around C$ 416.

Our data shows that Friday is the least expensive day to fly to Montreal. Tickets to fly out on this day can be as low as C$ 254. When flying out on a Wednesday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Montreal for around C$ 679.

Our data shows that the cheapest Chicago to Montreal flights are usually those with departure times in the afternoon. Our users have found flights to Montreal in the afternoon for as low as C$ 256. Flights in the morning are often more expensive with an average ticket price of C$ 488.

Fly from Chicago O'Hare Intl to Montreal Pierre Elliott Trudeau Intl for the best Chicago - Montreal flight prices

You are more likely to see cheaper flights to Montreal from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Montreal for around C$ 527 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Montreal from Chicago for as low as C$ 305 on momondo.

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

Historically, on average around 18% of flights between Chicago and Montreal have experienced a delay on any given week. The average delay length over the past 12 months has been 142 minutes.

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

Thursday is statistically the day of the week that experiences the fewest delays on this flight route. Wednesday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines has had the least delays on this route over the last 12 months, with about 13% of their flights experiencing any sort of delay.

As of February 2026, there are 18 flights per day flying from Chicago to Montreal. The most common time of day flights depart is 10:00a.m., with 57% of flights taking off at noon.

As of February 2026, 129 flights take off from Chicago and land in Montreal each week. The most common flight departure day for this route is Wed, with 16% of weekly flights taking off on this day.