This paper discusses the concept of toleration as it has been manifested in modern society through two contrasting processes—the prevalence of group identity, and the prevalence of identity defined according to citizenship and individual rights. Referring primarily to the work of political theorist Michael Walzer, the paper describes the historical development of toleration in the U.S., insofar as it is an immigrant nation which has passed through several phases of intolerance and toleration that continue to characterise the dynamics of American society, particularly in the city. Special reference is made to the city of Chicago, the largest city in the Midwest, where immigrants from all over settled, establishing ethnic neighbourhoods. Globalisation and  migration have made diversity a defining feature of contemporary society, and cities in particular. The multiplication of identities is being experienced on an individual level as well, giving rise to the recognition of the increasingly ‘hybrid’ nature of social and personal identification. The paper concludes by calling into question the implications of this post-modern model on the conceptualisation of toleration as well as its manifestations.