Correct option is B
(A) Chita: This city is located in eastern Siberia, Russia. (Matches with (III) Trans-Siberian Railway). The Trans-Siberian Railway connects Moscow in western Russia to Vladivostok in the east, passing through Chita.
(B) Winnipeg: This city is situated in central Canada. (Matches with (IV) Trans-Canadian Railway). The Trans-Canadian Railway stretches from Halifax on the Atlantic coast to Vancouver on the Pacific coast, with Winnipeg being a major stop along the way.
(C) Broken Hill: This city is located in western New South Wales, Australia. (Matches with (I) Australian Trans-Continental Railway). The Australian Trans-Continental Railway connects Sydney on the east coast to Perth on the west coast, passing near Broken Hill.
(D) Chicago: This city is a major transportation hub in the Midwestern United States. (Matches with (II) Union Pacific Railroad).