Cheap flights from Montreal to Chicago from $164

The month of February is, on average, the cheapest month to fly to Chicago from Montreal, with most prices found around $51. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Montreal to Chicago during October average around $52.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $431. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Montreal to Chicago for around $680.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Montreal to Chicago during this time can be as low as $509. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $571.

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

You are more likely to see cheaper flights to Chicago from Montreal when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $347 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Montreal for as low as $211 on momondo.

You could potentially save up to 1% on your flight if you consider stops on a Montreal to Chicago flight.

As of May 2026, prices for Montreal to Chicago flights are approximately 10% cheaper when compared to flights at the same time last year.

United Airlines, Air Canada, and Delta are the most popular carriers operating from Montreal to Chicago

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Montreal according to our data. Air Canada is the first choice among our users, with 74% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Toronto (YYZ) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Toronto (YYZ) offer the lowest average round-trip price of $279.

Flights connecting via Toronto (YTZ) have the shortest average one-way travel time: 4h 14m.

Toronto (YTZ) has the shortest average layover time for this route: 1h 01m.

26 flights are operational daily from Montreal to Chicago as of May 2026. The most popular departure time for this route is 9:00AM, with 47% of flights per day taking off at noon.

As of May 2026, 187 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Wed, with 15% of weekly flights taking off on this day.