This picture, which I lifted from the Chicago Tribune archives, looks like it was taken near North Avenue looking south toward North Michigan Avenue:
The shiny building in the center of the picture is Holabird & Root's iconic Palmolive Building, at the time one of the tallest skyscrapers in Chicago. It was built between 1927 and 1929 in high Art Deco style with soaring vertical lines, dramatic setbacks and a 97-foot tower topped by the Lindbergh Beacon, which could be seen all over the city and even by airplanes 225 miles away. The Arthur Rubloff Company renamed the burgeoning North Michigan Avenue shopping area the Magnificent Mile in the 1940s in an effort to brand it as a retail destination in consumers' minds. In 1967, the Palmolive Building was bought by Playboy magazine and became the Playboy Building. Two years later, Skidmore, Owings and Merrill built the John Hancock Center on the lot immediately behind the Playboy Building in this picture. At 1,127 feet, the Hancock Center dwarfed the once-mighty Playboy Building, and the beacon had to be turned off so it wouldn't shine directly into the Hancock's residential units. The building was rechristened the Palmolive Building in 2002 when it was converted to high-end condominiums and, of course, high-end retail shops.