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Agricultural land resources have been the central issue for the Chinese government in its attempts to secure food and agricultural sustainability. Yet strict land use control does not protect the agricultural land from erosion by urban expansion. Identifying the specific patterns and mechanisms of the agricultural land conversion, thus, is critical for land management and related decision making. Based on the annual nominal 30 m land use/land cover datasets (called CLUD-A), this study goes below the national/regional level to examine agricultural land conversion in Chongqing from a multiscale perspective. At the metropolis and its subdivision’s scales, the volume of the conversion area has been generally increasing, from 122.40 km2 in 1980–1990, 162.26 km2 in 1990–2000, and 706.14 km2 in 2000–2010, to 684.83 km2 in 2010–2015. Such a conversion in the main city area and its surroundings far outweighed that in the rural outskirts, as 68.9% (1990–2000), 92.2% (2000–2010), and 82.7% (2010–2015) of the conversion happened in the former. Moreover, values of Gini coefficients and coefficient of variation (CV) based on the county/district scale (Gini [0.46, 0.64], CV [0.69, 0.99] throughout the four periods) are much lower than those based on the town/village scale (Gini [0.88, 0.94], CV [3.18, 4.47] throughout the four periods), suggesting the uneven extent of spatial distribution of the agricultural land conversion trickles down along with the downscale of administration: the lower the administrative level, the more severe the unbalance. The policy rationale behind this transition is also discussed. This research argues for tangible approaches to a sustainable rural-urban transformation.