This article explores economic, cultural and political facets of ‘globalization’ through an analysis of the Olympic host city selection process. Rhetorical and statistical evidence illustrates that the Olympic bid process has become increasingly about demonstrating that one may be understood as a competitive global city. At the same time, the International Olympic Committee's ultimate decision also accounts for which city is the most locally distinctive. Furthermore, position and connectivity within global networks have ‘political’ ramifications that impact host selection. Ultimately, playing with the world's elite requires homogeneity in structural competency and networking potential across space, and simultaneous demonstration of maximal local qualitative difference. Consideration of Chicago's unsuccessful bid for the 2016 Games supports these conclusions. This empirical case study in glocalization reveals the logic behind Olympic host outcomes while demonstrating how place and difference remain crucial to today's ‘global’.