Flight tickets from Winnipeg to Chicago

If you’re looking for flight tickets from Winnipeg to Chicago, WestJet has exactly what you want. 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. 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. These are just some of the many reasons why Canadians book with WestJet and why you should too.

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Start your visit to Chi-town with WestJet

Airport Details: From YWG, Winnipeg James Armstrong Richardson 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.

Arrange your flight ticket now and start planning an exciting trip to Illinois's impressive, world-class destination. No matter the reason for your travel, you can rely on WestJet to get you from Winnipeg to Chicago so that you can enjoy Wrigley Field, Millennium Park and the Art Institute of Chicago.

Soar through the clouds with WestJet: book with us today.