In urban areas, deformation of transportation infrastructures may lead to serious safety accidents. Timely and accurate monitoring of the structural deformation is critical for prevention of transportation accidents and assurance of construction quality, particularly in areas with regional land subsidence, such as the city of Beijing. In this study, we proposed a method for the detection of seasonal deformation of highway overpasses using the integration of persistent scatterers Interferometric Synthetic Aperture Radar (PS-InSAR) techniques and seasonal indices, i.e., deformation concentration degree (DCD) and deformation concentration period (DCP) indices. Taking eastern Beijing urban area as a case study area, we first used the PS-InSAR technique to derive time series surface deformation based on 55 TerraSAR-X images during 2010–2016. Then, we proposed DCD and DCP indices to characterize seasonal deformation of 25 highway overpasses in the study area, with DCD representing to what degree the annual deformation is distributed in a year, and DCP representing the period on which deformation concentrates in the year. Our results showed that the maximum annual deformation rate reached −141.3 mm/year in Beijing urban area, and the PS-InSAR measurements agreed well with levelling measurements (R2 > 0.97). For PS pixels with DCD ≥ 0.3, the monthly deformation showed obvious seasonal patterns with deformation values during some months greater than those during the other months. DCP revealed that the settlement during autumn and winter was more serious than that in spring and summer. The seasonal patterns seemed to be related to the location, structure, and construction age of the overpasses. The upper-level overpasses, the newly constructed overpasses, and those located in the subsidence area (rate < −40 mm/year) tended to show a greater seasonal pattern. The seasonal deformation variations were also affected by groundwater-level fluctuation, temperature, and compressible layer.