Flights to Chicago from Winnipeg

If it's flights to Chicago from Winnipeg you're seeking, you can turn to WestJet. We fly into Chicago O’Hare International Airport and more than 150 other destinations across Canada, the U.S., Central America, the Caribbean and Europe — so you can depend on us to get you there. 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. So make your next trip one to remember and book with WestJet.

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We'll get you to Chi-town

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

Chicago is a true world city, known far and wide for its top-class museums and its assortment of diverse, culture-filled neighbourhoods. Known as the birthplace of the modern building, Chi-Town is not only home to some of the most unique looking buildings, but also some of the most innovative and influential architectural designs. Of course, no trip here is complete without watching one of the famous Second City comedy shows or ordering one of the city's most famous exports – deep-dish pizza.

Isn't it about time you took a trip? Book flights now through WestJet and you'll be jetting off to impressive, world-class Chicago in no time. Whether your itinerary is all business or all fun — including the likes of Wrigley Field, Millennium Park or the Art Institute of Chicago — we make it easy to get there swiftly, safely, comfortably and affordably. Fly to Chicago from Winnipeg with WestJet and enjoy the journey along the way.

Your next journey starts now: book with WestJet today.