Route Price Intelligence
Cheap Flights From Chicago to Winnipeg
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$697
Great Deal
Under $682
Typical Range
$682 – $734
Lowest We've Seen
$251
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$677
Feb
$710
Mar
$732
Apr
$691
May
$697
Jun
$697
Jul
$697
Aug
$697
Sep
$593
Oct
$513
Nov
$633
Dec
$678
Cheapest Average Expensive
Best Time to Fly from Chicago to Winnipeg
The cheapest time to fly from Chicago to Winnipeg is typically October, when fares average around $513. The most expensive month tends to be March at around $732. For the best deals, consider flying in October, September, November.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: November9,961 fares analyzedTypical low: $757
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