Direct flights from Calgary to Chicago

Make WestJet your first and last stop in your search for direct flights from Calgary to Chicago. We operate scheduled flights to more than 100 destinations in North America, Central America, the Caribbean and Europe — including Chicago O’Hare International Airport — and we make it our mission to get you wherever you need to be. Because one of our main priorities has always been to provide superior guests experiences, you can trust that you’ll always have a safe, affordable trip. So start by checking out our direct flights today.

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Get your ticket to Chi-town from WestJet

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

Chicago is an economic powerhouse, a cultural hub and one of the most popular city destinations in the United States. Here in "Chi-town," visitors have at their disposal a huge range of pastimes and attractions, from the entertainment-filled Navy Pier to the world-class retail experiences on State Street and the Magnificent Mile. And the city's most recognized cuisine, the deep-dish pizza, is on offer at pizzerias and restaurants all over the city.

You can always trust in WestJet for direct flights when you want to experience a truly impressive and world-class destination in Illinois. Enjoy swift, comfortable travel from Calgary to Chicago with WestJet and put Wrigley Field, Millennium Park and the Art Institute of Chicago right at your fingertips.

For a safe, comfortable and caring air travel experience, book with WestJet.