Cheap flights from Chicago to Winnipeg
Compare hundreds of airlines Chicago–Winnipeg
Live fares from 100+ sites — free, with no hidden fees.
About this route
Compare flights from Chicago to Winnipeg, a about 1,154 km route (around 1h 57m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as Air Canada, United Airlines operate this route.
How to get the best price
Airlines on this route
FAQ
What's the cheapest month to fly Chicago to Winnipeg?
Prices vary by season; use the price calendar to find the cheapest month.
How long is the flight from Chicago to Winnipeg?
A nonstop flight takes about 1h 57m and covers around 1,154 km. Connecting itineraries take longer.
Are there direct flights from Chicago to Winnipeg?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Chicago to Winnipeg?
Air Canada, United Airlines operate this route, among others. Compare them all in the results.
When should I book Chicago–Winnipeg flights?
As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.
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Chicago → Winnipeg · Live fares from 100+ sites — free, with no hidden fees.