Geometric structures for all the possible isomers of fluorinated pyridines were optimized at the B3LYP/6-311++G(d,p) level of theory. Aromaticities of the considered molecules were investigated using different indices included geometry-based (HOMA and Bird [I (6)]), magnetism-based (NICS(1) and diamagnetic susceptibility anisotropy [Delta chi]), pi- and sigma-electron count-based (pEDA, sEDA), and recently introduced electronic-based (electric field gradient [EFG(0), EFG(0.5)] and Shannon aromaticity) indices. Moreover, we used also HOMO-LUMO gap, atomization energy (D (0)), and interaction energy for fluorinated pyridine complexes by water molecule as global descriptors, and the EFG values (EFG(C-F)(0)) on the middle points of C-F bonds and sigma-electron population (N (sigma)) of nitrogen atom as local descriptors. All studied indices except HOMA and EFG(0.5) are well correlated to each other and to global and local descriptors.