Parking lots have wide variety of shapes because of surrounding environment and the objects inside the parking lot, such as trees, manholes, etc. In the case of paving the parking lot, as much area as possible should be covered by the construction vehicle to reduce the need for manual workforce. Thus, the coverage path planning (CPP) problem is formulated. The CPP of the parking lots is a complex problem with constraints regarding various issues, such as dimensions of the construction vehicle and data processing time and resources. A strategy based on convolutional neural networks (CNNs) for the fast estimation of the CPP’s average track length, standard deviation of track lengths, and number of tracks was suggested in this article. Two datasets of different complexity were generated to analyze the suggested approach. The first case represented a simple case with a working polygon constructed out of several rectangles with applied shear and rotation transformations. The second case represented a complex geometry generated out of rectangles and ellipses, narrow construction area, and obstacles. The results were compared with the linear regression models, with the area of the working polygon as an input. For both generated datasets, the strategy to use an approximator to estimate outcomes led to more accurate results compared to the respective linear regression models. The suggested approach enables us to have rough estimates of a large number of geometries in a short period of time and organize the working process, for example, planning construction time and price, choosing the best decomposition of the working polygon, etc.