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 Chicago airfares from $552/RT are provided by Cheapoair.com. Outbound flight is leaving on 01/28/2025, 12:45 pm from Winnipeg Intl (YWG) airport and arrives at Chicago Midway (MDW) at 05:47 pm. The flight time is 5 hours and 2 minutes. The Returning flight departes on 02/12/2025, 06:59 pm (other return dates are also available). Date posted: 07 Dec 2024
Price evolution for flights From Winnipeg To Chicago
Recent Deals on Flights from Winnipeg to Chicago:Roundtrip / Oneway
- $552
Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 01/28/2025 12:45 pm Chicago, IL (MDW) Winnipeg, MB (YWG) 02/12/2025 06:59 pm - $558
Porter Airlines
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 12/28/2024 07:00 pm Chicago, IL (MDW) Winnipeg, MB (YWG) 01/05/2025 11:15 am - $562 Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (ORD) 01/28/2025 05:00 am Chicago, IL (ORD) Winnipeg, MB (YWG) 02/12/2025 06:59 pm - $646
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 01/28/2025 07:00 pm Chicago, IL (MDW) Winnipeg, MB (YWG) 02/12/2025 07:45 am - $826 Porter Airlines
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 12/29/2024 05:00 am Chicago, IL (MDW) Winnipeg, MB (YWG) 01/04/2025 11:25 am - $336 Porter Airlines
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 01/02/2025 07:00 pm - $496 Westjet
cheapoair.com check priceFrom To Departure Time Winnipeg, MB (YWG) Chicago, IL (MDW) 01/02/2025 12:20 pm
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Know what to do when flying to Chicago?
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