Airline tickets to Chicago from Winnipeg

When you're looking to find airline tickets to Chicago from Winnipeg, WestJet is your reliable resource. 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 there's more to us than just great destinations; we're also known for offering outstanding customer service and a safe, comfortable and affordable air travel experience. So, when service and value are important factors for your next trip, choose WestJet.

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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. No trip here is complete without experiencing two of the city's most famous exports — live comedy and deep dish pizza.

Ready to make your move? Book airline tickets with WestJet and before long you'll find yourself in impressive, world-class Chicago. It doesn't matter if it's business travel or a trip to see Wrigley Field, Millennium Park or the Art Institute of Chicago — you can get there with us. Fly to Chicago from Winnipeg with us and see how far a great guest experience can go.

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