Cheap flights from Vancouver Intl Airport to Chicago from C$ 263

The month of November is another great option to travel to Chicago, with average flight prices from Vancouver Intl Airport averaging around C$ 564.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 711. 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$ 961. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

In the evening is the cheapest time of day to fly from Vancouver Intl Airport to Chicago when you can find flight prices for as low as C$ 724. Flying to Chicago in the evening 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$ 883 per ticket.

Fly from Vancouver Intl to Chicago O'Hare Intl for the best Vancouver Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Vancouver Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 660 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Vancouver Intl Airport for as low as C$ 164 on momondo.

There are 4 cabin classes available to choose from on Vancouver Intl Airport 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 Vancouver Intl Airport to Chicago flight.

As of September 2026, prices for Vancouver Intl Airport to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

Alaska Airlines, Porter Airlines, and United Airlines are the most popular carriers operating from Vancouver Intl to Chicago

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Vancouver Intl Airport according to our data. Air Canada is the first choice among our users, with 58% 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.

Calgary (YYC) was the most common stop: 65% of momondo users choosing one-stop flights on this route connected there.

Flights via Calgary (YYC) offer the lowest average round-trip price of C$ 355.

Flights connecting via Seattle (SEA) have the shortest average one-way travel time: 6h 25m.

Denver (DEN) has the shortest average layover time for this route: 1h 02m.

The number of flights available between Vancouver Intl Airport and Chicago is 10 per day as of September 2026. The most frequent departure time is 1:00p.m., with 53% of daily flights leaving in the afternoon.

The number of flights available between Vancouver Intl Airport and Chicago is 76 per week as of September 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.