The Chicago Tribune Tower competition was one of the largest, most important and most controversial design contests of the 1920s. The international competition generated 263 entries for the design of the new Tribune office building, and they represented a broad constellation of approaches to the skyscraper at a time of transition. In the decades following the competition, the design entries have often been evaluated in terms of the rise and demise of particular conceptions of modernism. This study examines the various contexts in which the Chicago Tribune Tower design competition took place and how they shaped the event. Analyzing how the competition contributed to changing concepts of the skyscraper, it also demonstrates how it engaged with the production of consumer culture, with conflicts of national identity and cultural unity, and with a newspaper's efforts to produce a civic and corporate icon during the turbulent years following World War I.