It is essential to create organic compounds that exhibit circularly polarized luminescence (CPL) in the near‐infrared (NIR) range. Helicene‐type emitters possess appealing chiroptical features, however, such NIR molecules are scarce due to a paucity of synthetic strategies. Herein, we developed a series of helical β‐isoindigo‐based B−O−B bridged aza‐BODIPY analogs that were synthesized conveniently. The reaction of diimino‐β‐isoindigo with a heteroaromatic amine produced a restricted ligand cavity, which triggered off the generation of a B−O−B bridge. The B−O−B bridge led to distorted conformations that satisfy the helical requirements, resulting in excellent spectroscopic and chiroptical properties. Tunable CPL with the highest luminescence dissymmetry factor (glum) of 1.3×10−3 and a CPL brightness (BCPL=11.5 M−1 cm−1) in the NIR region was achieved. This synthetic approach is expected to offer a new opportunity to chiral chemistry and increase flexibility for chiroptical tuning.