Round trip flights to Chicago from Winnipeg
If it's round trip flights to Chicago from Winnipeg you're seeking, you can turn to WestJet. You may be pleased to know Chicago O’Hare International Airport isn't the only place we land; we're also proud to offer flights to more than 150 exciting destinations in Canada, the U.S., Mexico, Central America, the Caribbean and Europe. But we don't simply get you from Point A to Point B; at WestJet, we make it our mission to provide caring, courteous service and the safest flight possible — all at an incredible value. So if you want great value without sacrificing great service, turn to WestJet.
Low fare finder
Don't see what you're looking for? Find all of our great low fares in one place.
Your journey to Chi-town starts with us
Airport Details: To ORD, Chicago O’Hare International Airport From YWG, Winnipeg James Armstrong Richardson International Airport
Travellers looking for a world-class city with a beautiful lakefront and abundant green space are never disappointed in Chicago. Fans of architecture are drawn to Chicago because it's the birthplace of the modern building, its skyline marked by instantly recognizable structures. Innovative brickwork aside, it's two other Chicagoan classics that draw visitors all year round: side-splitting live comedy and the world's best deep dish pizza pies.
So why wait? Browse and book round trip flights with WestJet now and make your trip to impressive, world-class Chicago a reality. Whether you're excited to visit such coveted attractions as Wrigley Field, Millennium Park and the Art Institute of Chicago, or you're simply travelling for business, you can be sure that you can get there with WestJet. Fly to Chicago from Winnipeg with WestJet, the airline that gives you more for less.