#62 Sun-Times Daily News Building (now the site of the Trump Tower), 1965

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Sun-Times Daily News Building (now the site of the Trump Tower), 1965

This 1965 nighttime photograph captures the Sun-Times Daily News building aglow with office lights, its long modern façade reflected in the dark river below. A prominent rooftop sign reads “CHICAGO SUN-TIMES” and “CHICAGO DAILY NEWS,” anchoring the scene as a vivid piece of mid-century Chicago media and architecture.

Seen from the waterline, the image emphasizes the building’s horizontal lines, glassy windows, and the bustle suggested by illuminated interiors. The surrounding skyline hints at a downtown in transition, with high-rise towers rising nearby and the riverfront serving as a dramatic foreground.

Now known as the site of the Trump Tower, this historical photo offers a striking before-and-after look at a famous Chicago riverfront location. It’s a compelling glimpse into the city’s newspaper era and a reminder of how quickly urban landscapes can change while the river remains a constant backdrop.