Route Price Intelligence
Cheap Flights From Chicago to Winnipeg
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$658
Deals From
$576
Usually Costs
$576 – $758
Lowest We've Seen
$251
Based on 6,650 price pointshigh confidence
Monthly Price Guide
Jan
$758
Feb
$771
Mar
$964
Apr
$642
May
$535
Jun
$628
Jul
$613
Aug
$596
Sep
$585
Oct
$757
Nov
$758
Dec
$758
Cheapest Average Expensive
Best Time to Fly from Chicago to Winnipeg
The cheapest time to fly from Chicago to Winnipeg is typically May, when fares average around $535. The most expensive month tends to be March at around $964. For the best deals, consider flying in May, September, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $25285 price checksWorst: $611