Route Price Intelligence
Cheap Flights From Chicago to Winnipeg
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 6d ago
$371Incredible deal to Canada's prairie gem! Nonstop WestJet flights to Winnipeg for just $371 - that's 53% below the typical price. Perfect for exploring Manitoba's cultural heart and gateway to the Canadian wilderness.
✓ 8 date combinations found at this price
Search Google FlightsTypical Price
$636
Deals From
$478
Usually Costs
$478 – $801
Lowest We've Seen
$251
Based on 2,408 price pointshigh confidence
Monthly Price Guide
Jan
$801
Feb
—
Mar
—
Apr
$810
May
$523
Jun
$540
Jul
$568
Aug
$478
Sep
$474
Oct
$801
Nov
$801
Dec
$801
Cheapest Average Expensive
Best Time to Fly from Chicago to Winnipeg
The cheapest time to fly from Chicago to Winnipeg is typically September, when fares average around $474. The most expensive month tends to be April at around $810. For the best deals, consider flying in September, August, May.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $25366 price checksWorst: $611