Last minute flight deals from Chicago to Winnipeg

For last minute flight deals from Chicago to Winnipeg, WestJet has what you’re looking for. We operate scheduled flights to more than 100 destinations in North America, Central America, the Caribbean and Europe — including Winnipeg James Armstrong Richardson International Airport — and we make it our mission to get you wherever you need to be. Our mission is to provide our guests with great experiences, which for many means safe and affordable travel. Book your next getaway with us today.

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Get your ticket to The Peg from WestJet

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

As Canada's second-sunniest city, Winnipeg radiates a warm and welcoming vibe; it's also home to a diverse array of attractions, from exceptional ballet and opera productions to exquisite lakes and parks. The Peg also enjoys a reputation as a city with a diverse and exciting calendar of events, from the Winnipeg Comedy Festival to Festival du Voyageur. 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.

Arrange your last minute flight deal now and start planning an exciting trip to Manitoba's spirited, sociable destination. We know Assiniboine Park, The Forks National Historic Site and The Manitoba Museum are amongst the things you can’t wait to see, which is why at WestJet, we’re dedicated to getting you from Chicago to Winnipeg.

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