This paper presents a computer vision-based approach to chronic subdural hematoma segmentation that can be performed by one click. Chronic subdural hematoma is estimated to occur in 0.002–0.02% of the general population each year and the risk increases with age, with a high frequency of about 0.05–0.06% in people aged 70 years and above. In our research, we developed our own dataset, which includes 53 series of CT scans collected from 21 patients with one or two hematomas. Based on the dataset, we trained two neural network models based on U-Net architecture to automate the manual segmentation process. One of the models performed segmentation based only on the current frame, while the other additionally processed multiple adjacent images to provide context, a technique that is more similar to the behavior of a doctor. We used a 10-fold cross-validation technique to better estimate the developed models’ efficiency. We used the Dice metric for segmentation accuracy estimation, which was 0.77. Also, for testing our approach, we used scans from five additional patients who did not form part of the dataset, and created a scenario in which three medical experts carried out a hematoma segmentation before we carried out segmentation using our best model. We developed the OsiriX DICOM Viewer plugin to implement our solution into the segmentation process. We compared the segmentation time, which was more than seven times faster using the one-click approach, and the experts agreed that the segmentation quality was acceptable for clinical usage.