Various aromatic polybenzoxazole (PBO) films were prepared through the two‐step silylation method by low‐temperature solution polycondensation of trimethylsilyl‐substituted bis(o‐aminophenol)s with aromatic dicarboxylic acid chlorides yielding precursor poly(o‐trimethylsiloxy‐amide)s, followed by thermal cyclocondensation. Four aromatic PBOs had glass transition temperatures (Tg) in the range of 275–375°C, and the Tg values were slightly lower than those of the structurally related polyimides. The temperatures of 10% weight loss of these PBOs ranged from 545–615°C in nitrogen, and the values were somewhat higher than those of the structurally similar polyimides. The films of the PBOs had tensile strengths of 105–135 MPa, elongations at break of 11–25%, and tensile moduli of 2.1–2.8 GPa.