The report briefly introduces the major content of Metropolitan Chicago On to 2050，which was released in October 2018. The structure of this planning is very clear. First，based on comprehensive investigation and research，challenges are analyzed. Multiple interest parties are invited to discuss them. 3 applicable principles and 5 chapters are finalized，and digital thoughts will be used to follow their implementation. Different from traditional plannings，Chicago focuses on innovative thoughts to address its challenges. The way of rational analysis and innovative thoughts could provide lessons for Shanghai Metropolitan Area.