Cheap flights from Winnipeg to Chicago
from 176 US$
From 722 USD — compare hundreds of airlines
The cheapest month is usually 2026-09 · 176 US$
See prices for my dates →Live fares from 100+ sites — free, with no hidden fees.
About this route
Compare flights from Winnipeg to Chicago, 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.
When to buy and when to fly
Prices by date
Fares found by date — cheapest days in green.
How to get the best price
Airlines on this route
FAQ
What's the cheapest month to fly Winnipeg to Chicago?
It's usually 2026-09, from 176 USD. Use the price calendar to compare other dates.
How long is the flight from Winnipeg to Chicago?
A nonstop flight takes about 1h 57m and covers around 1,154 km. Connecting itineraries take longer.
Are there direct flights from Winnipeg to Chicago?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Winnipeg to Chicago?
Air Canada, United Airlines operate this route, among others. Compare them all in the results.
When should I book Winnipeg–Chicago 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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Winnipeg → Chicago · Live fares from 100+ sites — free, with no hidden fees.