The lack of cutting transportation during drilling operations especially in horizontal and inclined wells can lead to large amounts of non-productive time and costly solutions. This problem has been encountered very often in the field due mostly to settlement of the cuttings at the bottom side of the hole and especially around pipe joints. Moreover, adopted rheological models are limited to 60 deg. inclination angle to predict the flow behavior of cuttings transport in directional wells. Therefore, the objective of this paper is to investigate the effect of various parameters related to the well configuration (inclined vs. horizontal), operating conditions, pipe/tool joints configurations, and flow conditions on the cutting velocity through an extensive experimental study with data analytics. The experimental approach was analyzed through film software, which allowed for the cutting velocities to be estimated. Regression models of cutting velocity with respect to each dimensionless group were formed and validated through a statistical analysis. A new empirical model for the cutting velocity was developed using multiple linear regression analyses. A sensitivity analysis was conducted to highlight the contribution of each dimensionless group on the variation of the cutting velocity. The newly proposed model for cutting velocity was tested and the calculated cutting velocity of 0.532 ft/s (.162 m/s) fell within the range of study between 0.188 ft/s (.057 m/s) and 0.690 ft/s (.210 m/s).