Chongming Island, the third largest island in China, has experienced dramatic shoreline changes due to erosion, river deposits, and human activities. While previous studies have shown the capacity of Landsat series images to extract shoreline dynamics, the spatial variation of shoreline dynamics and their corresponding driving factors remain unclear. Therefore, we established a method to monitor the shoreline dynamics of Chongming Island from 1984 to 2020 and to evaluate the driving factors of shoreline changes using a novel approach to Landsat image analysis. The method, based on the LISA (local indicator of spatial autocorrelation) concept, automatically extracted the shoreline from Landsat imagery. The results show that the LISA method, based on the SWIR1 band, has a high capacity for shoreline extraction in Chongming Island. By distinguishing the responses of the eastern and northern shorelines to upstream sediment loads and comprehensively analyzing the driving factors of eastern and northern dynamics, we found that: (i) although upstream sediment loads decreased dramatically, the shoreline of Chongming Island is still expanding due to human activities (i.e., reclamation and an estuary project) and sediment re-suspension from near-shore or cross-shore currents; (ii) the expansion of Chongming Island was initially due to the dynamics at the eastern shoreline, but the expansion of the eastern shoreline slowed after 2008 as upstream sedimentation slowed, less construction of cofferdams took place, and the Qingcaosha Reservoir was constructed; (iii) the northern shoreline of Chongming Island expanded rapidly after 1999, due to the merger of Xinlongsha, Xincunsha, and Chongming Island, and the transport of coastal and offshore sediments by hydrodynamic processes; and (iv) the main driving factors of eastern shoreline movement on Chongming Island are cofferdam reclamation and coastal engineering, and the changes at the northern shoreline are mainly affected by reclamation projects, offshore sediment supplies, and upstream sediment inflow. The results of this study provide theoretical fundamentals for land reclamation and future urban planning for Chongming Island.