Find out what a flight from Calgary to Chicago Midway 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.

Best airport options between Calgary and Chicago

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

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

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Match your flight search to your preferences: Calgary – Chicago Midway

Jetcost makes it easy to find the right flight. Set filters for flight time, price, number of stops, and preferred airline. You’ll see offers from Expedia, Ryanair, British Airways, Easyjet, and more.

Other popular destinations

Thinking about traveling to United States? Other users also viewed: Atlanta, Los Angeles, Miami, New York City, Orlando.

Don’t forget to check change or cancellation policies, especially if your plans aren’t final. For a more targeted search, you can also set price limits directly in the filters.