Flight tickets from Chicago to Winnipeg

Make WestJet your first and last stop in your search for flight tickets from Chicago to Winnipeg. We fly to destinations in North America, Central America, the Caribbean and Europe — including flights into Winnipeg James Armstrong Richardson International Airport — and we're here to get you where you want to be. One of our main focuses is to provide our guests with great experiences, which include safe, affordable travel, and that will never change. Take a look at our range of flight tickets today.

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Plan your visit to The Peg with WestJet

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

When the sun shines above Winnipeg — and it often does, this being Canada's second-sunniest city — visitors are drawn to its natural surroundings, which consist of wetlands, prairies, forests and more. Manitoba's largest city, also known as The Peg, is also a hub for festivals, including the Red River Exhibition, Winnipeg Comedy Festival and Winnipeg Aboriginal Film Festival. You'll even find sandy beaches on the coast of Lake Winnipeg: at Grand Beach Provincial Park, visitors can go for a dip, stroll along the boardwalk or explore the sand dunes.

Your trip to Manitoba's most spirited and sociable destination starts when you book your flight ticket. Enjoy swift, comfortable travel from Chicago to Winnipeg with WestJet and put Assiniboine Park, The Forks National Historic Site and The Manitoba Museum right at your fingertips.

For a safe, comfortable and caring air travel experience, book with WestJet.