This study evaluated a deep neural network (DNN) algorithm for automated aortic diameter quantification and aortic dissection detection in chest computed tomography (CT). A total of 100 patients (median age: 67.0 [interquartile range 55.3/73.0] years; 60.0% male) with aortic aneurysm who underwent non-enhanced and contrast-enhanced electrocardiogram-gated chest CT were evaluated. All the DNN measurements were compared to manual assessment, overall and between the following subgroups: (1) ascending (AA) vs. descending aorta (DA); (2) non-obese vs. obese; (3) without vs. with aortic repair; (4) without vs. with aortic dissection. Furthermore, the presence of aortic dissection was determined (yes/no decision). The automated and manual diameters differed significantly (p < 0.05) but showed excellent correlation and agreement (r = 0.89; ICC = 0.94). The automated and manual values were similar in the AA group but significantly different in the DA group (p < 0.05), similar in obese but significantly different in non-obese patients (p < 0.05) and similar in patients without aortic repair or dissection but significantly different in cases with such pathological conditions (p < 0.05). However, in all the subgroups, the automated diameters showed strong correlation and agreement with the manual values (r > 0.84; ICC > 0.9). The accuracy, sensitivity and specificity of DNN-based aortic dissection detection were 92.1%, 88.1% and 95.7%, respectively. This DNN-based algorithm enabled accurate quantification of the largest aortic diameter and detection of aortic dissection in a heterogenous patient population with various aortic pathologies. This has the potential to enhance radiologists’ efficiency in clinical practice.