Chondrosarcoma (CHS) is a malignant tumor of soft tissue with cartilaginous differentiation that represent one tenth of all malignant proliferations developed from bone tissues. Even if CHS represents the third malignancy with bone localization, after myeloma and osteosarcoma, it is far less diagnosed in the head and neck region. The current paper presented two cases of conventional CHSs, which were diagnosed in Department of Thoracic Surgery and Department of Otorhinolaryngology of Emergency City Hospital, Timişoara, Romania, between February and June 2021. The malignant cases were of peripheral CHSs, one of scapula, and the other one had an extremely rare tracheal location with microscopic features of conventional low-grade tumors (grade 1). In all cases, conservative surgical curative treatment was performed, with a favorable postoperative evolution.