Direct flights from Winnipeg to Chicago
All flights from YWG to ORD non-stop. There are direct flights from Winnipeg International (YWG), Canada to Chicago O Hare International (ORD), Illinois, USA with United Airlines. 14 weekly departures are currently scheduled on this route. Departure times range from 07:00 to 14:15 depending on the schedule period. The flight distance is 709 miles (1141 km). Flight time ranges from 2 hours and 21 minutes to 2 hours and 35 minutes.
Winnipeg
, Canada
Chicago
, USA
Flight schedule from Winnipeg to Chicago with United Airlines
This is a weekly direct flight schedule for United Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-07-21
Winnipeg to Chicago scheduled departures
Select a date to see every published non-stop departure between YWG and ORD.
YWG - ORD route facts
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Distance709 miles (1141 km)
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Flight time2 hours and 21 minutes to 2 hours and 35 minutes
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Airline United
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Airline alliancesStar Alliance
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CabinsEconomy First
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Hub airportsORD (Largest hub.)
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Arrival terminalsTerminal 2
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AircraftEmbraer 175 (Enhanced Winglets)
Route FAQ
Direct flights from Winnipeg to USA
From Winnipeg to Fort Lauderdale
FLL Fort Lauderdale Hollywood International
From Winnipeg to Orlando
MCO Orlando International
From Winnipeg to Palm Springs
PSP Palm Springs International
From Winnipeg to Phoenix
PHX Phoenix Sky Harbor International
From Winnipeg to Las Vegas
LAS Harry Reid International Airport
From Winnipeg to Atlanta
ATL Hartsfield–Jackson Atlanta International Airport
From Winnipeg to Denver
DEN Denver International
From Winnipeg to Minneapolis
MSP Minneapolis St Paul International
