Aortic dissection is a life-threatening vascular disease associated with high rates of morbidity and mortality, especially in medically underserved communities. Understanding patients’ blood flow patterns is pivotal for informing evidence-based treatment as they greatly influence the disease outcome. The present study investigates the flow patterns in the false lumen of three aorta dissections (fully perfused, partially thrombosed, and fully thrombosed) in the chronic phase, and compares them to a healthy aorta. Three-dimensional geometries of aortic true and false lumens (TLs and FLs) are reconstructed through an ad hoc developed and minimally supervised image analysis procedure. Computational fluid dynamics (CFD) is performed through a finite volume unsteady Reynolds-averaged Navier–Stokes approach assuming rigid wall aortas, Newtonian and homogeneous fluid, and incompressible flow. In addition to flow kinematics, we focus on time-averaged wall shear stress and oscillatory shear index that are recognized risk factors for aneurysmal degeneration. Our analysis shows that partially thrombosed dissection is the most prone to false lumen degeneration. In all dissections, the arteries connected to the false lumen are generally poorly perfused. Further, both true and false lumens present higher turbulence levels than the healthy aorta, and critical stagnation points. Mesh sensitivity and a thorough comparison against literature data together support the reliability of the CFD methodology. Image-based CFD simulations are efficient tools to assess the possibility of aortic dissection to lead to aneurysmal degeneration, and provide new knowledge on the hemodynamic characteristics of dissected versus healthy aortas. Similar analyses should be routinely included in patient-specific hemodynamics investigations, to plan and design tailored therapeutic strategies, and to timely assess their effectiveness.