Understanding the process of settlement expansion and the spatiotemporal variation of driving forces is the foundation of rational and specific planning for sustainable development. However, little attention has been paid to the spatiotemporal differences of driving forces among different counties, especially when they are representatives of different development types. This study used Guanyun, Kunshan and Changshu as case studies, and binary logistic regression was employed. The results showed that the expansion rates of Kunshan and Changshu were 5.55 and 3.93 times higher than that of Guanyun. The combinations and relative importance of drivers varied with counties and periods. The change in the number of driving forces can be divided into three stages: increasing stage, decreasing stage, and stable stage. In the relatively developed counties, Kunshan and Changshu, the importance of population is decreased, while it remain an important factor in the less developed county, Guanyun. In addition, the effect of GDP stays the same in Kunshan while it becomes the most important factor in Changshu. The distance to the main road and the distance to town are increasingly important in Kunshan and Guanyun, and distance to town has been the only common factor in the last period, indicating the discrepancy is increased. The relative importance of distance to a lake in Kunshan and Changshu increased, reflecting the role of increasing tourism in accelerating settlement expansion.