Airline tickets from Chicago to Winnipeg

You can count on WestJet when it comes to airline tickets from Chicago to Winnipeg. 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. One of our main priorities has always been to offer our guests superior experiences; with us that means safe, affordable travel. So book with WestJet today.

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Let's fly to The Peg

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 city is perhaps most renowned for its roster of annual events, none of which are more prestigious than the famed Winnipeg Comedy Festival. The appeal of Manitoba's capital and largest city is rounded out by nearby Grand Beach Provincial Park, where great natural swimming, fishing and hiking facilities are available.

You can always trust in WestJet for airline tickets when you want to experience a truly spirited and sociable destination in Manitoba. 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.