Flights from Winnipeg to Chicago
Flights from Winnipeg to Chicago is what WestJet does best. We fly all over North America, Central America, the Caribbean and Europe, including Chicago O’Hare International Airport, so you can always rely on us to go to the destination you need to be. Our long-term commitment to great guest experiences and safe, affordable travel means our passengers pay less and get more. Take a look at our range of flights today.
Low fare finder
Don't see what you're looking for? Find all of our great low fares in one place.
WestJet has your ticket to Chi-town
Airport Details: From YWG, Winnipeg James Armstrong Richardson International Airport To ORD, Chicago O’Hare International Airport
Chicago is a major metropolis with a variety of claims to fame, chief among them being its trademark skyline and its vital contributions to comedy and music. In fact, "Chi-Town" gives its guests an almost inexhaustible list of things to see and do, whether it's care-free fun at Navy Pier or trips to the top of some of the world's tallest buildings. And no trip to the Windy City would be complete without biting into a deep-dish pizza, the city's celebrated dish.
Arrange your flight now and start planning an exciting trip to Illinois's impressive, world-class destination. Enjoy Wrigley Field, Millennium Park and the Art Institute of Chicago once you've experienced safe, swift air travel from Winnipeg to Chicago with WestJet.