Flights to Chicago from Calgary

If you're researching flights to Chicago from Calgary, you'll want to give WestJet a look. We fly to Chicago O’Hare International Airport and more than 150 destinations in Canada, the U.S., Mexico, the Caribbean and Europe, which means we can take you to wherever you want to go. But our great routes aren't the only thing we offer; we also provide an exceptional guest experience that includes safe, comfortable and sensibly-priced travel each and every time. Book your journey with WestJet today.

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Your flight to Chi-town begins here

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

Located on the shores of Lake Michigan in the heart of the Midwest is Chicago, a city that’s home to a collection of famous museums, beautiful lakefront parks, diverse neighbourhoods and attractions. Architecture plays a role in the city's appeal; in fact, Chi-Town is widely acknowledged as the origin of the modern building. The city is equally renowned for its steaming deep dish pizza and for hosting some of the best stand-up acts and venues anywhere in the world.

Ready to hit the skies? Book flights now through WestJet and you'll be jetting off to impressive, world-class Chicago in no time. Whether your itinerary is all business or all fun — including the likes of Wrigley Field, Millennium Park or the Art Institute of Chicago — we make it easy to get there swiftly, safely, comfortably and affordably. Fly to Chicago from Calgary with WestJet and make the most of a great guest experience.

For exceptional service at a great value, book with WestJet today.