Round trip flights from Winnipeg to Chicago

If you're considering your options for round trip flights from Winnipeg to Chicago, WestJet is the smart choice. Our wide and diverse network of flights includes stops into Chicago O’Hare International Airport, which makes us your go-to partner when you need to get where you're going. In addition, our commitment to safe, friendly and affordable air travel is second-to-none, so you can expect your money to go further with us. Book your next getaway with us today.

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Let's fly to Chi-town

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

Chicago is an economic powerhouse, a cultural hub and one of the most popular city destinations in the United States. 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.

Find round trip flights with WestJet that will take you to one of the most impressive and world-class places in Illinois. No matter the reason for your travel, you can rely on WestJet to get you from Winnipeg to Chicago so that you can enjoy Wrigley Field, Millennium Park and the Art Institute of Chicago.

Reach for the sky with WestJet: book your next flight with us today.