Find out what a flight from Calgary to Chicago might cost

Prices vary based on date, airline, and availability. Compare several options if you're flying between Calgary and Chicago.

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

What are the airport options between Calgary and Chicago?

If both departure and destination cities offer multiple airports, comparing them can help you save time and money.

• Airports in Calgary: Calgary is currently the only airport available.
• Airports in Chicago: 3 airports serve Chicago - Midway, O'Hare, Rockford.

Some airports have different terminals for low-cost and traditional airlines — knowing in advance can save time. You can filter results to see only the airports that suit you.

Flight filters for the route Calgary – Chicago

Customize your search on Jetcost to focus only on flights that suit your needs. Whether you want a direct connection, specific airline, or shorter layover, filters help you find it faster.

Other popular destinations

Flights to United States are often searched alongside: Atlanta, Los Angeles, Miami, New York City, Orlando.

The cheapest flights might leave at odd hours or arrive at less central airports — keep that in mind. If you travel often, you can always select your trusted airlines from the available options.