Flight deals to Winnipeg from Chicago
If it's flight deals to Winnipeg from Chicago you're seeking, you can turn to WestJet. We operate flights to more than 150 exciting destinations in North America, Central America, the Caribbean and Europe — which includes flights into Winnipeg James Armstrong Richardson International Airport — so you can rest assured that we're the airline that gets you where you want to be. Beyond our convenient routes, we believe in giving our passengers an outstanding experience from start to finish, which means you can expect air travel that's swift, safe, comfortable and affordable. So, when service and value are important factors for your next trip, choose WestJet.
Low fare finder
Don't see what you're looking for? Find all of our great low fares in one place.
Your trip to The Peg begins with WestJet
Airport Details: To YWG, Winnipeg James Armstrong Richardson International Airport From ORD, Chicago O'Hare International Airport
Often referred to as the "cultural cradle of Canada," Winnipeg is a great destination for anybody tempted by art, architecture and an action-packed calendar of annual events. It also enjoys a strong reputation for its exceptional golf courses, and during the winter months there are many opportunities to skate, ski and hike in the great outdoors. Manitoba's biggest city is also home to the famed Winnipeg Comedy Festival each and every year, giving guests the chance to enjoy some of the best stand-ups in the business.
Isn't it about time you took a trip? Book flight deals today through WestJet and your dream trip to spirited, sociable Winnipeg will quickly become a reality. Whether you're gearing up to enjoy coveted attractions like Assiniboine Park, The Forks National Historic Site and The Manitoba Museum or you're just taking a business trip, you can get there with WestJet. Fly to Winnipeg from Chicago and see how far you can go with WestJet.