Cheap flights from Vancouver to Chicago from $206

The month of October is, on average, the cheapest month to fly to Chicago from Vancouver, with most prices found around $250. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Vancouver to Chicago during September average around $285.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $423. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Vancouver to Chicago for around $653.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Vancouver to Chicago during this time can be as low as $472. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $508.

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 $422 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 $116 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.

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

Air Canada, United Airlines and American Airlines 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 45% of people opting to fly with this airline when traveling 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.

As of July 2026, 10 flights take off from Vancouver and land in Chicago each day. The most common flight departure time for this route is 1:00PM, with 44% of daily flights taking off in the afternoon.

The number of flights available between Vancouver and Chicago is 71 per week as of July 2026. The most frequent departure day is Thu, with 15% of weekly flights leaving on this day.