Flight deals from Calgary to Chicago

When it comes to finding flight deals from Calgary to Chicago, there’s no better place to look than WestJet. We operate flights to Chicago O’Hare International Airport and many other airports in Canada, the United States, Mexico and Caribbean, which makes us your number one source for a flight that's right. We believe in affordable travel and exceptional customer care, so our passengers can always expect to pay less and get more. So if we encompass the things you value most in flying then book with us today.

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Your visit to Chi-town starts with a WestJet ticket

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

Chicago is a truly unforgettable city, one known for its dynamic neighbourhoods, specialty cuisine, world championship sports teams and beautiful skyline. Once visitors touch down in "Chi-town," they'll quickly discover a vast array of attractions, including everything from the popular Lincoln Park Zoo and Shedd Aquarium to the designer boutiques along Michigan Avenue. There's also the city's signature dish to try: deep-dish pizza.

Rely on WestJet for flight deals when you want to visit one of the most impressive, world-class places in Illinois. We know Wrigley Field, Millennium Park and the Art Institute of Chicago are amongst the things you can’t wait to see, which is why at WestJet, we’re dedicated to getting you from Calgary to Chicago.

For an exceptional guest experience, book with WestJet today.