Cheap flights from Alberta to Chicago from $165

The month of February is, on average, the cheapest month to fly to Chicago from Alberta, with most prices found around $248. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Alberta to Chicago during May average around $273.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $421. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Alberta to Chicago for around $628.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Alberta to Chicago during this time can be as low as $382. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $723.

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

You are more likely to see cheaper flights to Chicago from Alberta when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $339 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Alberta for as low as $224 on momondo.

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

Delta and United Airlines are the most popular carriers operating from Alberta to Chicago

WestJet, United Airlines and Air Canada are the top three most popular airlines that fly to Chicago from Alberta according to our data. WestJet is the first choice among our users, with 36% of people opting to fly with this airline when traveling 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 October 2026, there are 3 flights per day flying from Alberta to Chicago. The most common time of day flights depart is 1:00PM, with 100% of flights taking off in the afternoon.

As of October 2026, 24 flights take off from Alberta and land in Chicago each week. The most common flight departure day for this route is Thu, with 42% of weekly flights taking off on this day.