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Extra virgin olive oils produced from three cultivars on different maturation stages were characterized using Raman spectroscopy. Chemometric methods (principal component analysis, discriminant analysis, principal component regression and partial least squares regression) applied to Raman spectral data were utilized to evaluate and quantify the statistical differences between cultivars and their ripening process. The models for predicting the peroxide value and free acidity of olive oils showed good calibration and prediction values and presented high coefficients of determination ( > 0.933). Both the R-2, and the correlation equations between the measured chemical parameters, and the values predicted by each approach are presented; these comprehend both PCR and PLS, used to assess SNV normalized Raman data, as well as first and second derivative of the spectra. This study demonstrates that a combination of Raman spectroscopy with multivariate analysis methods can be useful to predict rapidly olive oil chemical characteristics during the maturation process.