Crohn’s disease (CD) is a complex inflammatory bowel disease, defined by chronic transmural inflammation and marked heterogeneity in both anatomical distribution and disease behavior, with potential involvement of any segment of the gastrointestinal tract and multiple phenotypes. Advanced cross sectional imaging nowadays plays a central role in CD management, reliably assessing both luminal and extraluminal inflammatory manifestations, supporting initial diagnosis, phenotypic characterization, and longitudinal monitoring of disease activity, complications and treatment response. Over the last two decades, Intestinal Ultrasound (IUS), MR Enterography (MRE), and Computed Tomography Enterography (CTE) have become central components of the diagnostic pathway. MRE has emerged as the most comprehensive, radiation-free modality for evaluating intestinal extent, inflammatory activity, and complications in Crohn’s disease. Multiparametric MRE, combining T2-weighted imaging, contrast-enhanced sequences, diffusion-weighted imaging, and cine acquisitions, enables a real “Crohn’s disease staging”, namely a thorough evaluation of the transmural inflammation, of fibrotic and fistulizing lesions in the small and large bowel, like in the perianal region. IUS provides a dynamic, widely accessible, safe and repeatable imaging technique that is particularly well suited for tight-monitoring strategies, early assessment of therapeutic response, and routine follow-up, especially in experienced centers. Notably CTE, despite concerns related to cumulative ionizing radiation exposure, remains indispensable in acute clinical settings owing to its rapid acquisition, broad availability, and high diagnostic accuracy for detecting abscesses, perforation, and bowel obstruction. Combined, these three modalities offer a complementary and patient-tailored framework for optimal CD management. This review outlines the pathological complexity of Crohn’s disease, traces the evolution of imaging approaches, and provides a comparative overview highlighting the specific strengths and limitations of each modality.