Flight deals from Chicago to Calgary

If you've come to WestJet to find flight deals from Chicago to Calgary, you've already taken the first step on your journey. We fly to destinations in North America, Central America, the Caribbean and Europe — including flights into Calgary International Airport — and we're here to get you where you want to be. We also believe that our passengers shouldn't get less simply because they pay less, and that's why we're committed to offering affordable air travel that comes complete with exemplary customer service. Browse our flight deals today.

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Your getaway to Cowtown starts here

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

Calgary is a magnet for business travellers — but its long list of attractions also makes it a great choice for fun-filled city breaks. Best yet, WestJet lands conveniently close to the downtown core, so that you can start exploring the city sooner rather than later. In fact, it's easy to see why this is Canada's spiritual home, from the famed Calgary Stampede ("The Greatest Outdoor Show on Earth") to Calaway Park amusements, historic Lougheed House, WinSport's Canada Olympic Park and more.

Your trip to Alberta's most historic and cosmopolitan destination starts when you book your flight deal. Whether it's for business purposes or to see the likes of Calgary Zoo, the National Music Centre or Canada’s Sports Hall of Fame, WestJet offers air travel from Chicago to Calgary that's swift, safe and comfortable.

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