Round trip flights from Chicago to Winnipeg

If you’re looking for round trip flights from Chicago to Winnipeg, WestJet has exactly what you want. Our flights take off and land all across North America, Central America, the Caribbean and Europe, including Winnipeg James Armstrong Richardson International Airport, which is why you can rely on us to get you where you need to be. On top of that, we offer a winning combination of affordability and comfort, so you can expect to pay less and get more. So check out our round trip flights today. 

Low fare finder

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

You can get to The Peg with WestJet

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

As the second-sunniest city in Canada, Winnipeg shines bright with its diversity of attractions — including everything from beautiful prairies, forests and wetlands to some of the finest ballet, orchestra and opera productions around. The Peg, as it is affectionately called, is also known to host numerous outdoor festivals — the Winnipeg Comedy Festival, the Winnipeg International Jazz Festival and Festival du Voyageur, just to name a few. You'll even find sandy beaches on the coast of Lake Winnipeg: at Grand Beach Provincial Park, visitors can go for a dip, stroll along the boardwalk or explore the sand dunes.

Rely on WestJet for round trip flights when you want to visit one of the most spirited, sociable places in Manitoba. No matter the nature of your visit, you’re sure to enjoy Assiniboine Park, The Forks National Historic Site and The Manitoba Museum — most of all you can count on WestJet to get you from Chicago to Winnipeg.

For a safe, comfortable and caring air travel experience, book with WestJet.