In 1922, the Chicago Tribune hosted an international design competition for its new headquarters and offered a $50,000 prize for "the most beautiful and eye-catching building in the world". The competition worked brilliantly as a publicity stunt, and the resulting entries still reveal a unique turning point in American architectural history.

More than 260 entries were received.

The winner was a neo-Gothic design by Raymond Hood and John Howells with flying buttresses near the top. This was a relatively safe design tactic, with a Gothic-skyscraper precedent in Cass Gilbert's Woolworth Building of 1910.

The entry widely perceived as the best — a radically simplified tower by the Finnish architect Eliel Saarinen — took second place. Saarinen's tower, which anticipated the coming impact of stripped-down, honest modernism on building form, was preferred by critics like the great Louis Sullivan, and was a strong influence on the next generation of skyscrapers — including Raymond Hood's own subsequent work on the McGraw-Hill Building and Rockefeller Center. The 1929 Gulf Building in Houston, Texas is a full realization of that Saarinen design.

Other Tribune tower entries by figures like Walter Gropius, Bertram Goodhue, Bruno Taut , Adolf Loos remain intriguing suggestions of what might have been, but perhaps not as intriguing as the one surmounted by Rushmore-like head of an American Indian. These entries have been collected in The Chicago Tribune Tower Competition : Skyscraper Design and Cultural Change in the 1920s by Katherine Solomonson and Richard A. Etlin, 2001. In 1980 a number of architects including Robert A.M. Stern jokingly submitted "late entries".

Construction on the actual Tribune Tower was completed in 1925 and reached a height of 462 feet (141 meters) above ground. The buttresses surrounding the peak of the tower are especially telling when the tower is lit at night.

The tower features carved images of Robin Hood (Hood) and a howling dog (Howells) near the main entrance to commemorate the architects. Prior to the building of the Tribune Tower, correspondents for the Chicago Tribune reputedly brought back rocks and bricks from a variety of historically important sites throughout the world. Many of these reliefs have been incorporated into the lowest levels of the building and are labeled with their location of origin. These include the Taj Mahal, the Parthenon, Abraham Lincoln’s Tomb, the Great Wall of China and the Berlin Wall. In all, there are 136 fragments in the building. More recently a rock returned from the moon was embedded in the building.

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• Chicago Tribune tower