Parking space is usually very limited in major cities, especially Cairo, leading to traffic congestion, air pollution, and driver frustration. Existing car parking systems tend to tackle parking issues in a non-digitized manner. These systems require the drivers to search for an empty parking space with no guarantee of finding any wasting time, resources, and causing unnecessary congestion. To address these issues, this paper proposes a digitized parking system with a proof-of-concept implementation that combines multiple technological concepts into one solution with the advantages of using IoT for real-time tracking of parking availability. User authentication and automated payments are handled using a quick response (QR) code on entry and exit. Some experiments were done on real data collected for six different locations in Cairo via a live popular times library. Several machine learning models were investigated in order to estimate the occupancy rate of certain places. Moreover, a clear analysis of the differences in performance is illustrated with the final model deployed being XGboost. It has achieved the most efficient results with a R 2 score of 85.7%.