Pillars represent some of the commonest supporting elements of modern and historical buildings. Non-destructive testing methods can be applied to gain information about the status of these structural elements. Among them, ground penetrating radar (GPR) is a popular diagnostic tool for the assessment of concrete structures. Despite several theoretical and experimental studies on concrete structural evaluation by GPR have been reported, little work has been done so far in relation to pillars. Owing to their circular geometry, pillars are complex multi-scattering environments, which render the interpretation of the radar images very challenging. This paper deals with the application of radio frequency tomography as a non-destructive technique for imaging the inner structure of pillars. The main goal of the study is the assessment of the imaging performance that can be obtained in comparison to conventional ground penetrating radar exploiting a multi-monostatic configuration. Accordingly, potentialities and performance of multimonostatic and multiview/multistatic measurement configurations are herein investigated in the inverse scattering framework. For each measurement configuration, the regularized reconstruction of a pointlike target and the spectral content are evaluated. The data inversion is carried out by means of the Truncated Singular Value Decomposition scheme. Tomographic reconstructions based on full-wave synthetic data are shown to support the comparative analysis.