Flights from Chicago to Winnipeg

If you've come to WestJet to find flights from Chicago to Winnipeg, you've already taken the first step on your journey. We fly all over North America, Central America, the Caribbean and Europe, including Winnipeg James Armstrong Richardson International Airport, so you can always rely on us to go to the destination you need to be. On top of that, we offer a winning combination of affordability and comfort, so you can expect to pay less and get more. These are just some of the many reasons Canadians choose to fly with WestJet and why you should too.

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Escape to The Peg with WestJet

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

Winnipeg enjoys more than its fair share of sunshine, but it isn't just a welcoming climate that makes it attractive to visitors — there is also natural beauty in abundance and a selection of some of the province's best live entertainment venues. The Peg, as it is affectionately called, is also known to host numerous outdoor festivals — the Winnipeg Comedy Festival, the Winnipeg International Jazz Festival and Festival du Voyageur, just to name a few. What's more, a beautiful sandy beach is never far away; in fact, at Grand Beach Provincial Park, visitors can go swimming, fishing and hiking along the coast of Lake Winnipeg.

Your trip to Manitoba's most spirited and sociable destination starts when you book your flight. We know you’re looking forward to Assiniboine Park, The Forks National Historic Site and The Manitoba Museum, which is why WestJet is committed to getting you from Chicago to Winnipeg.

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