Flight tickets to Chicago from Winnipeg

For flight tickets to Chicago from Winnipeg, WestJet has you covered. 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. On top of our great routes, we're proud to provide our passengers with air travel that's truly safe, swift and comfortable, all at an affordable price. Book your journey with WestJet today.

Low fare finder

Don't see what you're looking for? Find all of our great low fares in one place.

Your trip to Chi-town starts here

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.

So what are you waiting for? Book flight tickets now and look forward to exploring impressive, world-class Chicago. Whether you're flying for business or to check out the city's hottest attractions — including everything from Wrigley Field and Millennium Park to the Art Institute of Chicago — rest assured that you can get there safely with WestJet. Fly to Chicago from Winnipeg and find out how your money goes further with WestJet.

Take a trip to remember: book with WestJet today.