Last minute flights from Chicago to Winnipeg

If it’s last minute flights from Chicago to Winnipeg you’re looking for, you’ve come to the right place. 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. Because one of our main priorities has always been to provide superior guests experiences, you can trust that you’ll always have a safe, affordable trip. These are just some of the many reasons why Canadians book with WestJet and why you should too.

Find your tickets to The Peg at WestJet

As one of the sunniest cities in the country, Winnipeg is a vibrant destination with a plethora of attractions to choose from, including scenic parks, renowned theatre productions and professional sporting events. But "The Peg" is perhaps best known for its fun-filled calendar of annual events, including the Winnipeg Comedy Festival, the Winnipeg International Jazz Festival and Festival du Voyageur. You can even find a white sand beach just outside the city: at Grand Beach Provincial Park, swimming areas, an expansive boardwalk and sand dunes are just waiting to be enjoyed.

Find last minute flights now and you'll soon be on your way to one of Manitoba's most spirited and sociable destinations. 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.

Search for great WestJet flights