Sustainable urban development requires the integration of environmental interests in urban planning. Although various methods of environmental assessment have been developed, plan outcomes are often disappointing due to the complex nature of decision-making in urban planning, which takes place in multiple arenas within multiple policy networks involving diverse stakeholders. We argue that the concept of ‘decision windows’ can structure this seemingly chaotic chain of interrelated decisions. First, explicitly considering the dynamics of the decision-making process, we further conceptualized decision windows as moments in an intricate web of substantively connected deliberative processes where issues are reframed within a decision-making arena, and interests may be linked within and across arenas. Adopting this perspective in two case studies, we then explored how decision windows arise, which factors determine their effectiveness and how their occurrence can be influenced so as to arrive at more sustainable solutions. We conclude that the integration of environmental interests in urban planning is highly dependent on the ability of the professionals involved to recognize and manipulate decision windows. Finally, we explore how decision windows may be opened.