Relapsing polychondritis (RP) is a rare systemic disease of unknown etiology with a recurrent course characterized by progressive generalized inflammation of the cartilage and other connective tissue, leading to its destruction. The clinical presentation of relapsing polychondritis is highly variable and depends on the disease duration, exacerbation frequency, localization, and the number of structures involved. The recurrent nature of the disease, accompanied by nonspecific symptoms and the absence of pathognomonic symptoms and methods of definitive diagnosis challenge the disease diagnosis. We present a description of our clinical cases of RP patients with difficulties in making a clinical diagnosis by medical specialists in the early stages of the disease with a delay in establishing a final diagnosis of up to 2 years. A chronic recurrent course of the disease is typical. The variety of RP clinical manifestations and the absence of specific diagnostic methods require an in-depth study of the past medical history and a comparison of clinical and diagnostic data on various organs and body systems. Raising the awareness of related medical specialists on the etiology, pathogenesis, and diagnostic criteria of RP will improve the early diagnosis of the disease and, consequently, improve the quality of medical care.