This historical/comparative dissertation focuses on three western suburbs of Chicago: Naperville, West Chicago, and Wheaton. This study answers three questions: how these communities began with similar features and arrived at very distinct outcomes in terms of population, wealth, prestige, character, and other traits; how suburbs, particularly railroad suburbs, mature over time; and how the interaction between these three towns and other suburbs influence their development. I draw upon three paradigms in urban sociology, the Chicago School, the political economy model, and the Los Angeles School, to answer these questions and develop an approach that emphasizes deep studies of small groups of suburbs due to their unique histories, character, and growth trajectories.