Cheap flights from Vancouver Intl Airport to Chicago from C$ 274

The month of September is another great option to travel to Chicago, with average flight prices from Vancouver Intl Airport averaging around C$ 630.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as C$ 724. 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$ 942. 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$ 726. 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$ 862 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$ 681 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$ 141 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.

No. A direct flight is the cheapest option for a flight between Vancouver Intl Airport to Chicago.

As of November 2026, prices for Vancouver Intl Airport to Chicago flights are approximately 39% more expensive when compared to flights at the same time last year.

Air Canada, United Airlines, and Delta 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 5 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: 61% 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 Denver (DEN) have the shortest average one-way travel time: 6h 26m.

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 4 per day as of November 2026. The most frequent departure time is 1:00p.m., with 55% of daily flights leaving in the afternoon.

The number of flights available between Vancouver Intl Airport and Chicago is 31 per week as of November 2026. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.