Route Price Intelligence
Cheap Flights From Chicago to Winnipeg
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$621
Deals From
$498
Usually Costs
$498 – $715
Lowest We've Seen
$251
Based on 8,035 price pointshigh confidence
Monthly Price Guide
Jan
$749
Feb
$569
Mar
$541
Apr
$446
May
$365
Jun
$524
Jul
$611
Aug
$675
Sep
$675
Oct
$705
Nov
$705
Dec
$678
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 $365. The most expensive month tends to be January at around $749. For the best deals, consider flying in May, April, June.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $25160 price checksWorst: $530