Background: Endometriosis is a chronic inflammatory condition characterized by the presence of endometrial tissue outside the uterus, which can cause pelvic pain, infertility, and other symptoms. The disease may manifest as superficial peritoneal or deep-infiltrating endometriosis or as ovarian endometriomas. Although the mechanisms associated with the regulation and production of inflammatory mediators in endometriosis have been widely investigated, the precise mechanism responsible for inflammation-induced pain remains unclear, and the findings related to the cytokine expression profile and the location of cytokines in cells are contradictory. The intensity of pain experienced by endometriosis patients is not proportional to the degree and severity of their disease. Pain has a significant impact on women suffering from endometriosis. Methods: The following inclusion criteria to the study were: presence of endometriomas vs teratomas, negative pregnancy test result, no prior obstetric and infertility treatment, and good health condition with no diseases or coagulation disorders. Blood samples were collected from all patients. The serum levels of chemokines were determined by ELISA. The Nottingham Health Profile (NHP) questionnaire was made. Results: The median serum levels of chemokines: Monocyte Chemoattractant Protein 1 (MCP-1) and Monocyte Chemoattractant Protein 3 (MCP-3) were statistically higher in the endometriomas group compared to the other two groups. In the NHP questionnaire the comparison of the subjective health dimensions in individual groups showed that the patients in the endometriomas group experienced a significantly higher intensity of “PAIN” compared to other groups. Correlation analysis between NHP dimensions and serum chemokine levels: spearman’s rank correlation analysis indicated a statistically significant relationship between the “VITAL ENERGY” dimension and the level of MCP-2 (r = –0.295; p = 0.022), MCP-3 (r = 0.254; p = 0.050), and RANTES (r = –0.353; p = 0.006); between the “EMOTIONS” dimension and the level of MCP-3 (r = 0.262; p = 0.043); and between the “INCONVENIENCE IN DAILY LIFE” dimension and the level of Eotaxin-1 (r = –0.283; p = 0.028) and CCL13 (r = –0.287; p = 0.026). Conclusions: The chemokines serum levels (i.e., MCP-1 and MCP-3) and intensity of “PAIN” were statistically higher in the endometriomas compared to the teratomas group of women. Therefore, understanding their role in endometriosis-related pain could help in the development of novel, multidisciplinary treatments.