Cheap flights to Winnipeg from Chicago

For cheap flights to Winnipeg from Chicago, WestJet has you covered. Whether you want to touch down at Winnipeg James Armstrong Richardson International Airport or you're considering travelling to one of our 150+ destinations in North America, Central America, the Caribbean or Europe, we can help your next trip take flight. But our extensive network of routes isn't the only thing that makes WestJet a great choice for travellers: we also offer a friendly, welcoming guest experience that helps to set our safe, affordable air travel apart. Get real value and unbeatable service for your next trip by flying with WestJet.

Your trip to The Peg starts here

Winnipeg is known as the “cultural cradle of Canada” for good reason, since it is home to a wide array of talented local artists, great architecture and fun-filled festivals. But it also draws outdoor adventurers with its facilities for golf, skiing, hiking and more. Manitoba's largest city is also one of its sunniest, so guests can often expect bright sunshine to accompany their visit to The Peg.

Are you ready to get away? Book cheap flights now with WestJet and soon you’ll be touching down in spirited, sociable Winnipeg. Whether you're flying for business or to check out the city's hottest attractions — including everything from Assiniboine Park and The Forks National Historic Site to The Manitoba Museum — rest assured that you can get there safely with WestJet. Fly to Winnipeg from Chicago with WestJet.

For exceptional service at a great value, book with WestJet today.

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