Flight deals from Winnipeg to Chicago

You can count on WestJet when it comes to flight deals from Winnipeg to Chicago. We fly to destinations in North America, Central America, the Caribbean and Europe — including flights into Chicago O’Hare International Airport — and we're here to get you where you want to be. One of our main priorities has always been to offer our guests superior experiences; with us that means safe, affordable travel. Take a look at our range of flight deals today.

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A WestJet ticket is the first step of your trip to Chi-town

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.

Find flight deals now and you'll soon be on your way to one of Illinois's most impressive and world-class destinations. Enjoy swift, comfortable travel from Winnipeg to Chicago with WestJet and put Wrigley Field, Millennium Park and the Art Institute of Chicago right at your fingertips.

For an enriching air travel experience, book with WestJet today.