While scholars have established the architectural influence of Second Empire Paris (1852-1870) on Chicago, few have investigated how the political and economic ideologies embodied in Haussmannization were adopted by the Burnham Plan of 1909, nor have they compared how those plans were received by affected populations. This paper positions Paris and Chicago both as cities connected by cultural exchange and as sites of comparison by analyzing two processes of modernization: urban planning and the annexation of suburban municipalities into the expanding cities. The collections of prominent Chicagoans in the Progressive Era (1889-1909) trace the influence of Paris’ renovation and establish the cities’ shared political and economic ideologies, including the prioritization of capital circulation and rationality over lived experience. Response to annexation is compared by analyzing residents’ statements from the industrial suburbs of La Villette and the Town of Lake given in 1) an official enquête carried out in 1859 by the Second Empire and 2) citywide and local newspapers that discuss Chicago’s 1889 process of annexation. This analysis finds that while cultural exchange between Paris and Chicago generated similar priorities and urban plans aimed at creating economic growth and unified—“civilized”—societies, suburban municipalities reacted to annexation processes by emphasizing the unique legal, economic, and social properties of their town, and viewed themselves as vital—but distinct—contributors to the central city’s existence. This paper concludes that while city planners responded to the exigencies of capitalist modernity with similar solutions, governmental structure and neighborhood-level particularities shaped how these plans were implemented and received.