Cheap flights from Chicago to Montreal from C$ 229

The cheapest month to fly to Montreal from Chicago is in October. Flight prices, which tend to average around C$ 78, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of October, then book flights to Montreal from Chicago during April instead. Flights to Montreal in April, while not as cheap as those in October, still average around C$ 90.

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$ 259. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Montreal for around C$ 606.

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$ 259. Flights in the morning are often more expensive with an average ticket price of C$ 540.

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$ 533 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$ 264 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.

You could potentially save up to 62% on your flight if you consider stops on a Chicago to Montreal flight.

As of June 2026, prices for Chicago to Montreal flights are approximately 33% cheaper when compared to flights at the same time last year.

Historically, on average around 19% 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 139 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing at night 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. Monday 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 14% of their flights experiencing any sort of delay.

As of June 2026, there are 28 flights per day flying from Chicago to Montreal. The most common time of day flights depart is 6:00p.m., with 39% of flights taking off in the afternoon.

As of June 2026, 202 flights take off from Chicago and land in Montreal each week. The most common flight departure day for this route is Sat, with 15% of weekly flights taking off on this day.