Harris Hawks Optimization (HHO) algorithm is a new metaheuristic algorithm, inspired by the cooperative behavior and chasing style of Harris' Hawks in nature called surprise pounce. HHO demonstrated promising results compared to other optimization methods. However, HHO suffers from local optima and population diversity drawbacks. To overcome these limitations and adapt it to solve feature selection problems, a novel metaheuristic optimizer, namely Chaotic Harris Hawks Optimization (CHHO), is proposed. Two main improvements are suggested to the standard HHO algorithm. The first improvement is to apply the chaotic maps at the initialization phase of HHO to enhance the population diversity in the search space. The second improvement is to use the Simulated Annealing (SA) algorithm to the current best solution to improve HHO exploitation. To validate the performance of the proposed algorithm, CHHO was applied on 14 medical benchmark datasets from the UCI machine learning repository. The proposed CHHO was compared with the original HHO and some famous and recent metaheuristics algorithms, containing Grasshopper Optimization Algorithm (GOA), Particle Swarm Optimization (PSO), Genetic Algorithm (GA), Butterfly Optimization Algorithm (BOA), and Ant Lion Optimizer (ALO). The used evaluation metrics include the number of selected features, classification accuracy, fitness values, Wilcoxon's statistical test (<inline-formula> <tex-math notation="LaTeX">P </tex-math></inline-formula>-value), and convergence curve. Based on the achieved results, CHHO confirms its superiority over the standard HHO algorithm and the other optimization algorithms on the majority of the medical datasets.