Drilling practice has been evolving parallel to the developments in the oil and gas industry. Current supply and demand for oil and gas dictate search for hydrocarbons either at much deeper and hard-to-reach fields, or at unconventional fields, both requiring extended reach wells, long horizontal sections, and 3D complex trajectories. Cuttings transport is one of the most challenging problems while drilling such wells, especially at mid-range inclinations. For many years, numerous studies have been conducted to address modeling of cuttings transport, estimation of the concentration of cuttings as well as pressure losses inside the wellbores, considering various drilling variables having influence on the process. However, such attempts, either mechanistic or empirical, have many limitations due to various simplifications and assumptions made during the development stage. Fluid thixotropy, temperature variations in the wellbore, uncertainty in pipe eccentricity as well as chaotic motion of cuttings due to pipe rotation, imperfections in the wellbore walls, variations in the size and shape of the cuttings, presence of tool joints on the drillstring, etc. causes the modeling of the problem extremely difficult. Due to the complexity of the process, the estimations are usually not very accurate, or not reliable. In this study, data-driven models are used to address the estimation of cuttings concentration and frictional loss estimation in a well during drilling operations, instead of using mechanistic or empirical methods. The selected models include Artificial Neural Networks, Random Forest, and AdaBoost. The training of the models is determined using the experimental data regarding cuttings transport tests collected in the last 40 years at The University of Tulsa – Drilling Research Projects, which includes a wide range of wellbore and pipe sizes, inclinations, ROPs, pipe rotation speeds, flow rates, fluid and cuttings properties. The evaluation of the models is conducted using Root Mean Square Error, R-Squared Values, and P-Value. As the inputs of the data-driven models, independent drilling variables are directly used. Also, as a second approach, dimensionless groups are developed based on these independent drilling variables, and these dimensionless groups are used as the inputs of the models. Moreover, performance of the data-driven model results are compared with the results of a conventional mechanistic model. It is observed that in many cases, data-driven models perform significantly better than the mechanistic model, which provides a very promising direction to consider for real time drilling optimization and automation. It is also concluded that using the independent drilling variables directly as the model inputs provided more accurate results when compared with dimensional groups are used as the model inputs.