An effcient, yet accurate, computational protocol for predicting nitrogen NMR chemical shifts based on density functional theory and the gauge-including atomic orbital approach has been proposed. A database of small and relatively rigid compounds containing nitrogen atoms was compiled. Scaling factors for the linear correlation between experimental 15N chemical shifts and calculated isotropic shielding constants have been systematically investigated with seven different levels of theory in both chloroform and dimethyl sulfoxide, two commonly used solvents for NMR experiments. The best method yields a root-mean-square deviation of about 5.30 ppm and 7.00 ppm in CHCl3 and DMSO, respectively. Moreover, another set of scaling factors for -NH2 chemical shifts was also proposed based on a separate database with three levels of theory. Furthermore, it is encouraging that a reasonable transferability for the linear correlation has been found between these two solvents. This finding will enable broader applications of the developed empirical scaling factors to other commonly used solvents in NMR experiments. The consistency between theoretical predictions and experimental results for structural elucidations was illustrated for selected examples including regioisomers, tautomers, oxidation states, and protonated structures.