Winnipeg → Chicago
Flights from Winnipeg to Chicago
Winnipeg
Chicago
Nonstop flights link Winnipeg and Chicago.
- Nonstop flight
- United Airlines (UA5639)
- Nonstop fare seen
- from £527 one way
- Straight-line distance
- 1,155 km
Searched and booked on Aviasales. Head Your Way may earn a commission at no extra cost to you.
What this is based on
Arrive inChicago →- The fare was in the fare provider's listings when read on 2 Oct 2026 and is a past price, not a quote.
- Source: Fare search by Travelpayouts, 2 Oct 2026. How Head Your Way works.
Continue from Chicago
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Browse direct connections
Airports: Chicago Meigs Airport (CGX); Chicago Midway International Airport (MDW); Chicago O'Hare International Airport (ORD), 26 km away; Chicago Executive Airport (PWK), 36 km away · Stations: Chicago Union Station; Chicago OTC; LaSalle Street; Millennium Station and 4 more · Ports: Chicago
Journeys through Chicago
Other ways to leave Winnipeg