Despite the public favour gained in Europe, interculturalism is often reduced to its theoretical abstractions or local implementations. There is scarce evidence to suggest that interculturalism mitigates the systemic discrimination of immigrant-origin people. Looking at the Italian case, the paper analyses the coexistence of interculturalism and discrimination into multicultural schools, examining school track choices for immigrant-origin students under the lens of interculturalism. We combine three theoretical perspectives—discrimination at micro level, critical interculturalism and school choice as a process—with an empirical analysis of qualitative data, focussing on the ambivalent relational mechanisms underneath the most discriminatory turning point in the Italian education system, the transition to upper secondary school. Different forms of student–teacher interaction, approaches to school track choice and discriminatory effects are highlighted in the research findings. Three different scenarios of interculturalism are identified and implemented through the negotiation of the school actors. Rethinking interculturalism by deconstructing discrimination appears as a collective task, to be undertaken together with teachers and students with immigrant background: intercultural policy guidelines must be combined with bottom-up actions.