Cheap flights from Winnipeg to Chicago

When it comes to finding cheap flights from Winnipeg to Chicago, there’s no better place to look than WestJet. 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. We’re committed to providing our guests with the best possible experiences, with safe, affordable and friendly travel. Explore our selection of cheap flights now.

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Plan 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 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.

Find the cheap flight you need to start planning an unforgettable visit to one of the most impressive and world-class destinations in Illinois. Enjoy swift, safe air travel from Winnipeg to Chicago with WestJet — and then get down to the serious business of enjoying the likes of Wrigley Field, Millennium Park or the Art Institute of Chicago.

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