Urbanization extensively modifies surface roughness and properties, impacting regional climate and hydrological cycles. Urban effects on temperature and precipitation have drawn considerable attention. These associated physical processes are also closely linked to clouds’ formation and dynamics. Cloud is one of the critical components in regulating urban hydrometeorological cycles but remains less understood in urban-atmospheric systems. We analyzed satellite-derived cloud patterns spanning two decades over 447 US cities and quantified the urban-influenced cloud patterns diurnally and seasonally. The systematic assessment suggests that most cities experience enhanced daytime cloud cover in both summer and winter; nocturnal cloud enhancement prevails in summer by 5.8%, while there is modest cloud suppression in winter nights. Statistically linking the cloud patterns with city properties, geographic locations, and climate backgrounds, we found that larger city size and stronger surface heating are primarily responsible for summer local cloud enhancement diurnally. Moisture and energy background control the urban cloud cover anomalies seasonally. Under strong mesoscale circulations induced by terrains and land–water contrasts, urban clouds exhibit considerable nighttime enhancement during warm seasons, which is relevant to strong urban surface heating interacting with these circulations, but other local and climate impacts remain complicated and inconclusive. Our research unveils extensive urban influences on local cloud patterns, but the effects are diverse depending on time, location, and city properties. The comprehensive observational study on urban–cloud interactions calls for more in-depth research on urban cloud life cycles and their radiative and hydrologic implications under the urban warming context.