Route Price Intelligence
Cheap Flights From Chicago to Winnipeg
Live pricing benchmarks, monthly patterns, and historical lows for this route.
🔥 Fire DealFound 2d 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
$647
Deals From
$515
Usually Costs
$515 – $801
Lowest We've Seen
$251
Based on 3,285 price pointshigh confidence
Monthly Price Guide
Jan
$801
Feb
$800
Mar
$805
Apr
$796
May
$534
Jun
$588
Jul
$598
Aug
$544
Sep
$504
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 $504. The most expensive month tends to be March at around $805. For the best deals, consider flying in September, May, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $25370 price checksWorst: $611