How much is a flight from Chicago to Winnipeg?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Winnipeg.

Pick a travel date to see today’s available fares.

Fares change often — checking several times throughout the week can make a big difference. Booking in advance often means access to lower prices for the Chicago - Winnipeg route.

Flying between Chicago and Winnipeg? Consider these airports

Depending on your destination and where you’re starting from, it might make sense to look beyond the main hubs.

• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
• Airports in Winnipeg: The only active option is Winnipeg.

Check if your destination airport has a rail link — it can make getting around easier. Jetcost lets you view options from all Chicago airports in a single search.

Choose the right flight for your trip from Chicago to Winnipeg

Jetcost helps you tailor your flight search based on what matters to you — flight length, budget, airline, or agency. Whether you prefer round-trip or one-way, direct or with stopovers, you’ll see options from the best airlines and travel agencies.

Other popular destinations

Flying to Canada? Many users also explore: Calgary, Edmonton, Montreal, Toronto, Vancouver.

Looking for a specific airline? Select it directly in the filters to speed up your search. The search filters help you see only the options that match your needs.