Purpose: To determine whether food texture affects chewing side preference (CSP) and to investigate the relationship between CSP and masticatory factors, such as occlusal contact area, bite force, and masticatory performance. Materials and Methods: Forty-seven adults (20 women and 27 men; mean age: 24 years) participated in this study. Three types of food (chewing gum, beef jerky, and peanuts) were provided to assess CSP. Occlusal contact area was measured at various ranges of interocclusal distance, and the bite force was measured. Masticatory performance was assessed according to the median particle size. Asymmetry indices of each measurement were calculated and analyzed using Pearson correlation coefficient (α = .05). Results: The CSP for beef jerky and peanuts were significantly correlated with each other, whereas the CSP for chewing gum was not correlated with other food. The proportion of participants who chewed equally on both sides was higher for chewing gum than for beef jerky. There was a significant correlation between the CSP for beef jerky and occlusal contact area, especially at interocclusal distance ranges of 0 to 89 μm and 0 to 109 μm (r = 0.41). Bite force and masticatory performance were not significantly correlated with CSP. Conclusions: Food texture seemed to affect CSP, and masticatory laterality was greater for tough foods. Moreover, CSP for tough food was closely related to the occlusal contact area at an interocclusal distance level of about 0.1 mm.