Cheap flights from Calgary to Chicago

Cheap flights from Calgary to Chicago is what WestJet does best. We fly all over North America, Central America, the Caribbean and Europe, including Chicago O’Hare International Airport, so you can always rely on us to go to the destination you need to be. Our long-term commitment to great guest experiences and safe, affordable travel means our passengers pay less and get more. Take a look at our range of cheap flights today.

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WestJet has your ticket to Chi-town

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. 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. There's also the city's trademark dish to sample: deep-dish pizza pie.

Arrange your cheap flight now and start planning an exciting trip to Illinois's impressive, world-class destination. Enjoy Wrigley Field, Millennium Park and the Art Institute of Chicago once you've experienced safe, swift air travel from Calgary to Chicago with WestJet.

For an exceptional guest experience, book with WestJet today.