Nonstop flights from Winnipeg to Chicago
United Airlines flies this route twice a day.
YWGWinnipeg Richardson International
706 mi · 14 flights a week
ORDChicago O'Hare International
When they leave
Winnipeg time7:00a2:00pFirst departure 7:00 AM, last 2:00 PM
One morning flight at 7:00 AM, then one afternoon flight at 2:00 PM. Every flight runs daily.
Every flight
Earliest first
Schedules last checked Sep 19, 2026. Times are local.
Flying from Winnipeg to Chicago
United Airlines is the only airline flying nonstop from Winnipeg to Chicago, twice a day on the Embraer 175.
The first arrival in Chicago is at 9:35 AM and the last at 4:35 PM. The flight covers 706 miles.
Flying back, Chicago to Winnipeg has 12 nonstop flights a week.
Return flights
More from Winnipeg
Find the cheapest day to fly from Winnipeg to Chicago.
Schedules as of Oct 9, 2026.