This paper examines Italo Calvino’s Invisible Cities as a unique literary canvas to reformulate the relationship between narratives and planning practices. It does so from the vantage point of the Frame, namely, the dialogues between the Khan (the planner) and Marco Polo (the resident/traveler) punctuating the imaginary cities described in the book. Read through with the aid of narratological concepts, the Frame functions a mini-treatise on urban complexity, structured along nine dyads of oppositional concepts (e.g., chaos vs. meaning; reality vs. possibility), which call into question as many planning milestones (e.g., control, purpose, model, balance), fostering an original reflection on the limitations and potentials of planning practices.