Flight Routes from Chicago to Winnipeg

Compare cheap outbound and return flights from Chicago (CHI) to Winnipeg (YWG) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
16x / week
Flight distance
1,161 km
Time difference
none
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Chicago (CHI) to Winnipeg (YWG)

Select a travel date in the flight schedule for the route from Chicago (CHI) to Winnipeg (YWG) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsCHI–YWG · 5 of 5
fromto
dep.arr.
durationstopovers
  1. September 13 – 19, 2026
  2. September 20 – 26, 2026
  3. Sep 27 – Oct 3, 2026
    1. ORDYWG
      nonstop
      1. United Airlines
    2. ORDYWG
      nonstop
      1. United Airlines
    3. ORDYWG
      nonstop
      1. United Airlines
    4. ORDYWG
      nonstop
      1. United Airlines
    5. ORDYWG
      nonstop
      1. United Airlines

      Important flight information

      Discover more flights around Chicago and Winnipeg

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport Winnipeg International (YWG)
      Destination country Flights to Canada
      Departure airport - Destination country Chicago-IL, all airports - Canada
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