Flight Routes from Winnipeg to Chicago O'Hare

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

Trip type
Cheapest roundtrip flight
from€595
Flight distance
1,139 km
Time difference

Cheap flight offers from Winnipeg to Chicago O'Hare

sorted by price and recency
filters
  1. –
    United Airlines
    –
    YWG–ORD
    non-stop flight
    United Airlines
    –
    ORD–YWG
    non-stop flight
    €654
  2. –
    Air Canada
    –
    YWG–ORD
    1 stopover
    Air Canada
    –
    ORD–YWG
    1 stopover
    €755
  3. –
    Air Canada
    –
    YWG–ORD
    1 stopover
    Air Canada
    –
    ORD–YWG
    1 stopover
    €684
  4. –
    Air Canada
    –
    YWG–ORD
    non-stop flight
    Air Transat
    –
    ORD–YWG
    1 stopover
    €658

Flight schedule from Winnipeg (YWG) to Chicago O'Hare (ORD)

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

offers
Active filtersnone
Matching outbound flightsYWG–ORD · 2 of 2
fromto
dep.arr.
durationstopovers
  1. November 22 – 28, 2026
  2. Nov 29 – Dec 5, 2026
  3. December 6 – 12, 2026
    1. YWGORD
      nonstop
      1. United Airlines
    2. YWGORD
      nonstop
      1. United Airlines

      Important flight information

      Discover more flights around Winnipeg and Chicago O'Hare

      Departure airport Airport Winnipeg International (YWG)
      Departure country Flights from Canada
      Arrival airport Airport Chicago O'Hare International Airport, IL (ORD)
      Destination country Flights to United States
      Departure country - Arrival airport Canada - Chicago O'Hare International Airport, IL
      Departure airport - Destination country Winnipeg International - United States
      Departure airport - City-Code Winnipeg International - Chicago
      Alternative routes to United States
      Alternative flights to Chicago O'Hare
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