CFD modeling using RANS and LES of pollutant dispersion in a three-dimensional street canyon is investigated by comparison with measurements. The purpose of this study is to confirm the accuracy of LES in modeling plume dispersion in a simple street canyon model and to clarify the mechanism of the discrepancy in relation to RANS computation. Simple LES modeling is shown by comparison with wind tunnel experiments to give better results than conventional RANS computation (RNG) modeling of the distribution of mean concentration. The horizontal diffusion of concentration is well reproduced by LES, mainly due to the reproduction of unsteady concentration fluctuations in the street canyon.