Tires, conveyor belts, floor mats, and shoe soles form a main-stream of rubber waste. The amount of these used materials continuously increases due to development of the rubber market. Therefore, pro-ecological utilization (i.e., energy recycling instead of burning) and recovering valuable and recyclable materials becomes an urgent necessity. In this regard, this work was devoted to the chemical recycling of selected used rubber products, and it especially explores the possibility of limonene production. Different types of waste rubber were characterized and pyrolyzed at microgram and laboratory scales, and the results were compared. Additionally, the pyrolysis of tires, the most significant stream of rubber waste, was also conducted in a semi-technical scale reactor. The effectiveness of limonene formation in the liquid fractions obtained from different types of waste rubber was compared.