Separation bubble and conical vortices on a large-span flat roof were observed in this study through the use of flow visualization. The results indicated that separation bubble occurred when the flow was normal to the leading edge of the flat roof. Conical vortices that occur under the cornering flow were observed near the leading edge, and their appearance was influenced by the wind angle. When the wind changed from along the diagonal to deviating from the diagonal of the roof, the conical vortex close to the approaching flow changed from circular to be more oblong shaped. Based on the measured velocities in the conical vortices by flow visualization, a proposed two-dimensional vortex model was improved and validated by simplifying the velocity profile between the vortex and the potential flow region. Through measured velocities and parameters of vortices, the intensities of conical vortices and separation bubble on a large-span flat roof under different wind directions were provided. The quasi-steady theory was corrected by including the effect of vortices. With this improved two-dimensional vortex model and the corrected quasi-steady theory, the mean and peak suction beneath the cores of the conical vortices and separation bubble can be predicted, and these were verified by measured pressures on a larger-scale model of the flat roof.