Cheap flights from Winnipeg to Chicago

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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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From $287 / RT details

Book your flight now with Flightnetwork and save!

Cheap Chicago airfares from $287/RT are provided by Flightnetwork. Outbound flight is leaving on 04/29/2020, 05:31 pm from Winnipeg Intl (YWG) airport and arrives at Chicago O`hare (ORD) at 08:00 pm. The flight time is 2 hours and 29 minutes. The Returning flight departes on 05/06/2020, 10:00 am (other return dates are also available). Date posted: 19 Mar 2020

Price evolution for flights From Winnipeg To Chicago

Price overview for flights from Winnipeg to Chicago

Recent Deals on Flights from Winnipeg to Chicago:Roundtrip / Oneway

  • $287Air Canada flight Air Canada 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/29/202005:31 pm
    Chicago, IL (ORD)Winnipeg, MB (YWG)05/06/202010:00 am
    flightnetwork.com check price
  • $287Air Canada flight Air Canada 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/29/202005:31 pm
    Chicago, IL (ORD)Winnipeg, MB (YWG)05/06/202010:00 am
    flyfar.ca check price
  • $478Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/29/202005:31 pm
    Chicago, IL (ORD)Winnipeg, MB (YWG)05/06/202007:30 am
    flightnetwork.com check price
  • $478Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/29/202005:31 pm
    Chicago, IL (ORD)Winnipeg, MB (YWG)05/06/202007:30 am
    flyfar.ca check price
  • $514Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/17/202005:00 am
    Chicago, IL (ORD)Winnipeg, MB (YWG)04/26/202008:00 am
    cheapoair.com check price
  • $152Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/27/202003:40 pm
    cheapoair.com check price
  • $168Air Canada flight Air Canada 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/27/202007:15 am
    flyfar.ca check price
  • $168Air Canada flight Air Canada 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/27/202007:15 am
    flightnetwork.com check price
  • $299Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/27/202007:00 am
    flightnetwork.com check price
  • $299Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Winnipeg, MB (YWG)Chicago, IL (ORD)04/27/202007:00 am
    flyfar.ca check price
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Know what to do when flying to Chicago?

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