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<i>H. italicum</i> essential oil (EO) is one of the most popular ingredients utilized by the cosmetic industry, and it is also used as natural antioxidant and as a value-added ingredient in food products. The chemical composition of the EO <i>H. italicum</i> cultivated in Serbia was analyzed by gas chromatography–mass spectrometry. The quantitative structure–retention relationship was used to predict the retention indices of the EO constituents acquired by GC-MS data, applying five molecular descriptors selected by factor analysis and a genetic algorithm. Also, antimicrobial activity, and biological activity by four common antioxidant tests (DPPH and ABTS assays, reducing power, and β-carotene bleaching test), and in vitro antihyperglycemic and anti-inflammatory capacities were evaluated. A total of 70 EO constituents were detected, of which 17 (8.5%) could not be identified. The <i>H. italicum</i> EO in this study belonged to γ-curcumene chemotype. The coefficients of determination reached the value of 0.964, demonstrating that this model could be used for prediction purposes. All applied tests showed that <i>H. italicum</i> EO possesses good biological activity and an interesting chemical composition. Therefore, the EO of <i>H. italicum</i> grown in Serbia has a potential to be used in food, cosmetic, and pharmaceutical products.