Cheap flights from Chicago to Montreal from $99

The cheapest month to fly to Montreal from Chicago is in April. Flight prices, which tend to average around $284, are often lower during this time because this is during the off-season. If you are unable to visit Montreal during the month of April, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $304.

The cheapest day to depart from Chicago to Montreal is on a Thursday when prices can be found for as low as $575. Flights from Chicago to Montreal on a Sunday will generally be more expensive and average around $787. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our most recent data shows that the best time of day to fly to Montreal is at noon. Flights from Chicago to Montreal during this time can be as low as $559. In the afternoon is when there is more demand to fly to Montreal, so prices are often more expensive at around $740 per ticket.

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 $385 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 $223 on momondo.

There are 4 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.

No. A direct flight is the cheapest option for a flight between Chicago to Montreal.

As of February 2026, prices for Chicago to Montreal flights are approximately 26% cheaper when compared to flights at the same time last year.

American Airlines, Porter Airlines, and Air Canada are the most popular carriers operating from Chicago to Montreal

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Montreal from Chicago according to our data. Air Canada is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Montreal. Keep in mind that there are 4 different airlines that fly to Montreal on a routine basis, so you have a few additional options to choose from.

Historically, on average around 17% 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 in the early afternoon have, in the past, seen delays more frequently in comparison.

Thursday 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, American Airlines 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.

Toronto (YTZ) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

Flights via Toronto (YYZ) offer the lowest average round-trip price of $307.

Flights connecting via Toronto (YTZ) have the shortest average one-way travel time: 4h 05m.

Toronto (YTZ) has the shortest average layover time for this route: 1h 05m.

As of February 2026, 20 flights take off from Chicago and land in Montreal each day. The most common flight departure time for this route is 10:00AM, with 56% of daily flights taking off at noon.

146 flights are operational weekly from Chicago to Montreal as of February 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.