Route Price Intelligence
Cheap Flights From Chicago to Winnipeg
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$726
Great Deal
Under $625
Typical Range
$625 – $811
Lowest We've Seen
$251
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$691
Feb
$746
Mar
$811
Apr
$794
May
$890
Jun
—
Jul
—
Aug
$1,011
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 August at around $1,011. 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: September22,754 fares analyzedTypical low: $674