Cheap flights from Chicago to Winnipeg
If you're searching for cheap flights from Chicago to Winnipeg, look no further than WestJet. We have flights to 100 destinations in North America, Central America, the Caribbean and Europe, including Winnipeg James Armstrong Richardson International Airport, so you’ll never have a problem getting where you need be, when you need to be there. Our long-term commitment to great guest experiences and safe, affordable travel means our passengers pay less and get more. Browse our cheap flights today.
Low fare finder
Don't see what you're looking for? Find all of our great low fares in one place.
Your getaway to The Peg starts here
Airport Details: From ORD, Chicago O'Hare International Airport To YWG, Winnipeg James Armstrong Richardson International Airport
As one of Canada's sunniest cities, Winnipeg is home to a brilliant array of attractions — from expansive parks and diverse neighbourhoods to celebrated ballet, opera and theatre productions. But The Peg's top attraction is its rich annual calendar of events, from the hilarious Winnipeg Comedy Festival to the ever-popular Festival du Voyageur, to name just a couple. 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.
Find cheap flights with WestJet that will take you to one of the most spirited and sociable places in Manitoba. Get the best out of Assiniboine Park, The Forks National Historic Site, The Manitoba Museum and more once you've flown from Chicago to Winnipeg with WestJet.