Leaf chlorophyll content is an important indicator of the health status of pear trees. This study used Korla fragrant pears, a Xinjiang regional product, to investigate methods for estimating the relative chlorophyll content of pear leaves. Samples were collected from pear trees in the east, south, west, and north positions of peripheral canopy leaves. The leaf soil plant analysis development (SPAD) method was implemented using a SPAD-502 laser chlorophyll meter. The instrument measures the relative chlorophyll content as the SPAD value. Leaf spectra were acquired using a portable field spectrometer, ASD FieldSpec4. ViewSpecPro 6.2 software was employed to smooth the ground spectral data. Traditional mathematical transformations and the discrete wavelet transform were used to process the spectral data, then correlation analysis was employed to extract the sensitive bands, and partial least squares regression (PLS) was used to establish a model for estimating the chlorophyll content of pear tree leaves. The findings indicate that (1) the models developed using the discrete wavelet transform had coefficients of determination (R²) exceeding 0.65, and their predictive performance surpassed that of other models employing various mathematical transformations, and (2) the model constructed using the L1 scale for the discrete wavelet transform had greater estimation accuracy and stability than models established through traditional mathematical transformations or the high-frequency scale for discrete wavelet transform, with an R² value of 0.742 and a root mean square error (RMSE) of 0.936. The prediction model for relative chlorophyll content established in this study was more accurate for chlorophyll monitoring in pear trees, and thus, it provided a new method for rapid estimation. Moreover, the model provides an important theoretical basis for the efficient management of pear trees.