Does life in the city foster mistrust of others? This study tests four connected hypotheses about urban mistrust by comparing the City of Chicago to suburbs, small cities, towns, and rural areas. The Urban Mistrust Hypothesis is that urban residents are more mistrusting than residents of places outside the city. The Neighborhood Disadvantage Hypothesis is that mistrust increases with the prevalence of economic and social disadvantage in one's neighborhood, which accounts for some of the mistrust associated with urban residence. The Individual Disadvantage Hypothesis is that socioeconomically disadvantaged individuals are more mistrusting than others, which accounts for some of the mistrust associated with residence in Chicago and in disadvantaged neighborhoods. The Neighborhood Disorder Hypothesis is that mistrust correlates positively with observing signs of disorder in one's neighborhood such as graffiti, vandalism, run-down or abandoned buildings, noise, crime, and people hanging out on the streets, drinking, or taking drugs; and disorder mediates some of the effects of residence in the city and in a disadvantaged neighborhood. Some, but not all, of the association between disorder and mistrust is mediated by criminal victimization. We examine these hypotheses using the Community, Crime and Health data, which is a 1995 survey of a representative sample of 2,482 Illinois residents linked to contextual data on their neighborhoods. We find results consistent with all four hypotheses. The mean level of mistrust reported by residents of Chicago is more than half a standard deviation above that of people living elsewhere. Most of the higher mistrust in Chicago can be attributed to three related things: neighborhood disadvantage, individual disadvantage, and neighborhood disorder; but even with adjustments for disadvantage and disorder, urban residents report more mistrust.