Chondrosarcomas are malignant neoplasms of mesenchymal origin and represent a heterogeneous group of tumors ranging from indolent, low-grade lesions to aggressive, high-grade neoplasms. The early diagnosis and treatment of chondrosarcomas is paramount to achieving a better prognosis. Multiple imaging modalities have been used for the purpose of initial detection, characterization, and staging, as well as for the performance of image-guided biopsies. As imaging techniques continue to evolve, radiologists are assuming an increasingly important role in the management of chondrosarcomas. This review describes the imaging characteristics of chondrosarcomas on multiple modalities and emphasizes the imaging features that may assist in differentiating these tumors from their benign counterparts, enchondromas and osteochondromas, which frequently still pose challenging diagnostic dilemmas.