This study investigated chemosensory degradations of soybean and canola oils with repeated frying in order to estimate the quality of the oils. Methods: Chemical parameters including oxygen induction time, acid value, p-anisidine value, malondialdehyde, and total polar compounds were measured. Electronic nose and electronic tongue analyses were performed to assess sensory properties. Multivariate analyses were employed to investigate relationships among tastes and volatile compounds using principal component analysis (PCA) and Pearson’s correlation analysis. Results: All chemical parameters increased with repeated frying in both oils. Electronic nose analysis found ethyl butyrate, 2-heptenal, and 2,4-pentanedione as major volatiles for soybean oil and ethyl butyrate and linalool for canola oil. As the numbers of frying increased, all volatiles showed an increased concentration in various extents. In multivariate analyses, ethyl butyrate revealed strong positive correlations with sourness, umami, and sweetness, and umami showed strong positive correlations with sourness and saltiness (p < 0.05). PCA confirmed that in PC1 with 49% variance, sourness, saltiness, and umami were at similar rates while acetyl pyrazine, 2,4-pentadieone, and 1-octanol were found at similar rates. Canola oil was chemically more stable and less susceptible to deterioration in all chemical parameters compared to soybean oil, resulting in a relatively better quality oil when repeatedly fried. Conclusion: The results suggested that minimum repeated frying (5 times) degrades chemosensory characteristics of both oils, thereby compromising their quality. The findings of this study will be utilized as a foundation for quality control of fried foods in food industry, fried food development, and fast-food industry.