Cheap flights from Montreal to Chicago from C$ 233

The month of October is another great option to travel to Chicago, with average flight prices from Montreal averaging around C$ 72.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as C$ 716. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 1,069. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the afternoon is the cheapest time of day to fly from Montreal to Chicago when you can find flight prices for as low as C$ 736. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,174 per ticket.

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 C$ 484 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 C$ 310 on momondo.

There are 4 cabin classes available to choose from on Montreal to Chicago 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 11% on your flight if you consider stops on a Montreal to Chicago flight.

As of June 2026, prices for Montreal to Chicago flights are approximately 9% cheaper when compared to flights at the same time last year.

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

Air Canada, United Airlines and Porter 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 64% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Toronto (YTZ) was the most common stop: 91% of momondo users choosing one-stop flights on this route connected there.

Flights via Toronto (YTZ) offer the lowest average round-trip price of C$ 219.

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.

As of June 2026, 28 flights take off from Montreal and land in Chicago each day. The most common flight departure time for this route is 9:00a.m., with 52% of daily flights taking off in the afternoon.

As of June 2026, 197 flights take off from Montreal and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.