Cheap flights from Vancouver to Chicago from C$ 157

The month of September is another great option to travel to Chicago, with average flight prices from Vancouver averaging around C$ 391.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as C$ 583. 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 Saturday because tickets tend to average around C$ 811. 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 to Chicago when you can find flight prices for as low as C$ 571. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 687 per ticket.

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

You are more likely to see cheaper flights to Chicago from Vancouver when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 506 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Vancouver for as low as C$ 219 on momondo.

There are 4 cabin classes available to choose from on Vancouver to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

WestJet is the most popular carrier operating from Vancouver to Chicago

Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago from Vancouver according to our data. Air Canada is the first choice among our users, with 48% 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.

As of February 2026, there are 5 flights per day flying from Vancouver to Chicago. The most common time of day flights depart is 10:00a.m., with 100% of flights taking off at noon.

As of February 2026, 38 flights take off from Vancouver 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.