Flight deals to Chicago from Winnipeg

When you're on the lookout for flight deals to Chicago from Winnipeg, rest assured that you can get there with WestJet. You'll be pleased to discover that our aircraft fly to over 150 destinations in North America, Central America, the Caribbean and Europe, including Chicago O’Hare International Airport. 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. For service and value that soars above the rest, choose WestJet.

Low fare finder

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

Enjoy all Chi-town has to offer with WestJet

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

Chicago is a world-class city with a beautiful lakefront, green spaces and diverse neighbourhoods to explore. Chi-Town has a fine reputation in the world of architecture, and is even recognized as having given the modern building to the world. Yet it's two other famous Chicagoan exports that have visitors coming in their millions year after year: raucous live comedy and delicious deep dish pizza.

Ready to hit the skies? Book flight deals now with WestJet and soon you’ll be touching down in 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 with us and discover how we put exceptional customer care first.

For exceptional service at a great value, book with WestJet today.