Direct flights from Chicago to Winnipeg
All flights from ORD to YWG non-stop. There are direct flights from Chicago O Hare International, Illinois, USA to Winnipeg International (YWG), Canada every day of the week with United Airlines. The flight distance is 709 miles and the trip usually takes about 2 hours and 34 minutes.
Airlines with non-stop routes:

United Airlines
Flight schedule from Chicago to Winnipeg 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 2025-04-22
Chicago to Winnipeg flight departures
Select a date to see all scheduled flight departures between ORD to YWG.

ORD - YWG information
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Distance709 miles (1141 km)
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Flight time2 hours and 34 minutes
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Airlines
United
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AlliancesOne WorldSky TeamStar Alliance
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ClassesEconomyBusinessFirst Class
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United AircraftEmbraer 170 / 175 / 190 / 195
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Departure TerminalTerminal 2 (United)
Direct flights from Chicago to Canada

From Chicago to Vancouver
YVR Vancouver International Airport

From Chicago to Calgary
YYC Calgary International
From Chicago to Edmonton
YEG Edmonton International Airport
From Chicago to Halifax
YHZ Halifax International

From Chicago to Quebec
YQB Quebec Jean Lesage International

From Chicago to Montreal
YUL Pierre Elliott Trudeau International

From Chicago to Ottawa
YOW Ottawa Macdonald Cartier International

From Chicago to Toronto
YYZ Pearson International