Cheap flights from Winnipeg to Chicago
Travel > North America > United States > Winnipeg to Chicago flights
Check our current prices for flights from Winnipeg to Chicago. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Winnipeg to Chicago, you will need to run a search below.
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Cheap airfares from /OW are provided by . This flight is going on , from () airport and arrives to () at so it makes 0 hours and 0 minutes. This is a oneway flight. Date posted: 31 Dec 1969
Price evolution for flights From Winnipeg To Chicago
Recent Deals on Flights from Winnipeg to Chicago:Roundtrip / Oneway
- $216
Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (ORD) 06/11/2025 08:30 am - $337 Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 06/11/2025 08:50 am - $388
Porter Airlines
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 06/11/2025 05:00 am - We are sorry but currently there are no roundtrip offers for flights from Winnipeg to Chicago.
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Know what to do when flying to Chicago?
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