Cheap tickets to Chicago from Toronto

For cheap tickets to Chicago from Toronto, WestJet has you covered. We fly to more than 150 destinations in Canada, the U.S., Mexico, Central America, the Caribbean and Europe — including flights into Chicago O’Hare International Airport, so you can trust us to get you where you want to be. Beyond the irresistible destinations on offer, countless travellers choose WestJet time and again for our remarkable customer care, as well as our commitment to safety and comfort. So make your next trip one to remember and book with WestJet.

Low fare finder

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

Let us take you to Chi-town

Airport Details: To ORD, Chicago O’Hare International Airport From YYZ, Toronto Pearson International Airport

Those who visit Chicago find a world-class city with a beautiful waterfront and plenty of urban green spaces to enjoy. Chi-Town has a fine reputation in the world of architecture, and is even recognized as having given the modern building to the world. No-one should leave the "Windy City" without getting a taste of comedy and deep-dish pizza, two things Chicago has perfected.

Ready to make your move? Book cheap tickets now and look forward to exploring impressive, world-class Chicago. We're here to get you there swiftly and comfortably, whether it's for business purposes or to enjoy fantastic attractions like Wrigley Field, Millennium Park or the Art Institute of Chicago. Fly to Chicago from Toronto with WestJet and enjoy the journey along the way.

Your next journey starts now: book with WestJet today.