A dedicated software package that could semi-automatically assess differences in aortic maximal cross-sectional diameters from consecutive CT scans would most likely reduce the post-processing time and effort by the physicians. The aim of this study was to present and assess the quality of a new tool for the semi-automatic quantification of thoracic aorta dilation dimensions. Twenty-nine patients with two CTA scans of the thoracic aorta for which the official clinical report indicated an increase in aortic diameters were included in the study. Aortic maximal cross-sectional diameters of baseline and follow-up studies generated semi-automatically by the software were compared with corresponding manual measurements. The semi-automatic measurements were performed at seven landmarks defined on the baseline scan by two operators. Bias, Bland–Altman plots and intraclass correlation coefficients were calculated between the two methods and, for the semi-automatic software, also between two observers. The average time difference between the two scans of a single patient was 1188 ± 622 days. For the semi-automatic software, in 2 out of 29 patients, manual interaction was necessary; in the remaining 27 patients (93.1%), semi-automatic results were generated, demonstrating excellent intraclass correlation coefficients (all values ≥ 0.91) and small differences, especially for the proximal aortic arch (baseline: 0.19 ± 1.30 mm; follow-up: 0.44 ± 2.21 mm), the mid descending aorta (0.37 ± 1.64 mm; 0.37 ± 2.06 mm), and the diaphragm (0.30 ± 1.14 mm; 0.37 ± 1.80 mm). The inter-observer variability was low with all errors in diameters ≤ 1 mm, and intraclass correlation coefficients all ≥ 0.95. The semi-automatic tool decreased the processing time by 40% (13 vs. 22 min). In this work, a semi-automatic software package that allows the assessment of thoracic aorta diameters from baseline and follow-up CTs (and their differences), was presented, and demonstrated high accuracy and low inter-observer variability.