Chapter abstract: This chapter addresses how the city government, related offices, non-profit organizations, and activists have attempted to shift Chicago’s urban development towards environmental sustainability. The chapter first, discusses what Chicago has accomplished, second, defines sustainability, third, outlines Chicago’s deficiencies in achieving its sustainability goals, and finally, presents alternative visions of sustainability rooted in resistance and activism. This chapter asks to what extent sustainable development in Chicago is influenced by its business-as-usual neoliberal context and to what extent it is influenced by alternative activist ideas of environmental justice.