Airfare from Chicago to Winnipeg

Make WestJet your first and last stop in your search for airfare from Chicago to Winnipeg. We fly into more than 100 destinations in North America, Central America, the Caribbean and Europe — including Winnipeg James Armstrong Richardson International Airport — which means we're able to take you wherever you want to go. 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. Book your next getaway with us today.

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Start your visit to The Peg with WestJet

Airport Details: From ORD, Chicago O'Hare International Airport To YWG, Winnipeg James Armstrong Richardson International Airport

As the second-sunniest city in Canada, Winnipeg shines bright with its diversity of attractions — including everything from beautiful prairies, forests and wetlands to some of the finest ballet, orchestra and opera productions around. Affectionately dubbed The Peg, this large, culturally diverse metropolitan city is a popular destination for much-loved festivals, including Festival du Voyageur, the Winnipeg Jazz Festival and the Winnipeg Fringe Theatre Festival. In the summer months, Grand Beach Provincial Park is wildly popular, with guests enjoying swimming, fishing, hiking or just a well-earned afternoon of relaxation.

Rely on WestJet for airfare when you want to visit one of the most spirited, sociable places in Manitoba. No matter the reason for your travel, you can rely on WestJet to get you from Chicago to Winnipeg so that you can enjoy Assiniboine Park, The Forks National Historic Site and The Manitoba Museum.

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