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This paper examines three historical trends in which the relationship between art and urban design has found a distinctive character, each represented by a major figure. The first trend, reflected in the work of Camillo Sitte, advocates an urban design that follows the artistic principles of the past, giving priority to history. In the second trend, Raymond Unwin envisages urban design as a civic art that reflects civic life, thus giving priority to community. In the third trend, represented by Le Corbusier, urban design draws on engineering and technology, with the future of society as its priority. The changing combinations of these three trends have shaped the debates about the nature of urban design and its relationship with art, influencing its future direction.