Flights from Calgary to Chicago

If flights from Calgary to Chicago is what you’re looking for, coming to WestJet was a smart move. We fly to destinations in North America, Central America, the Caribbean and Europe — including flights into Chicago O’Hare International Airport — and we're here to get you where you want to be. Our long-term commitment to great guest experiences and safe, affordable travel means our passengers pay less and get more. Book your next getaway with us today.

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Let's fly to Chi-town

Airport Details: From YYC, Calgary International Airport To ORD, Chicago O’Hare International Airport

Chicago is a major metropolis with a variety of claims to fame, chief among them being its trademark skyline and its vital contributions to comedy and music. In fact, "Chi-Town" gives its guests an almost inexhaustible list of things to see and do, whether it's care-free fun at Navy Pier or trips to the top of some of the world's tallest buildings. And no trip to the Windy City would be complete without biting into a deep-dish pizza, the city's celebrated dish.

If you need flights to one of the most impressive and world-class destinations in Illinois, you know you can get there with WestJet. We know you’re looking forward to Wrigley Field, Millennium Park and the Art Institute of Chicago, which is why WestJet is committed to getting you from Calgary to Chicago.

Reach for the sky with WestJet: book your next flight with us today.