The ubiquitous deployment of monitoring devices in urban flow monitoring systems induces a significant cost for maintenance and operation. A technique is required to reduce the number of deployed devices, while preventing the degeneration of data accuracy and granularity. In this paper, we present an approach for inferring the real-time and fine-grained crowd flows throughout a city based on coarse-grained observations. This task exhibits two challenges: the spatial correlations between coarse- and fine-grained urban flows, and the complexities of external impacts. To tackle these issues, we develop a model entitled UrbanFM which consists of two major parts: 1) an inference network to generate fine-grained flow distributions from coarse-grained inputs that uses a feature extraction module and a novel distributional upsampling module; 2) a general fusion subnet to further boost the performance by considering the influence of different external factors. This structure provides outstanding effectiveness and efficiency for small scale upsampling. However, the single-pass upsampling used by UrbanFM is insufficient at higher upscaling rates. Therefore, we further present UrbanPy, a cascading model for progressive inference of fine-grained urban flows by decomposing the original tasks into multiple subtasks. Compared to UrbanFM, such an enhanced structure demonstrates favorable performance for larger-scale inference tasks.