The olive fly, Bactrocera oleae (Rossi), a serious threat to the olive crop worldwide, displays ovipositon preference for some olive cultivars but the causes are still unclear. In the present work, three Portuguese olive cultivars with different susceptibilities to olive fly (Cobrançosa, Madural, and Verdeal Transmontana) were studied, aiming to determine if the olive volatiles are implicated in this interaction. Olive volatiles were assessed by SPME-GC-MS in the three cultivars during maturation process to observe possible correlations with olive fly infestation levels. Overall, 34 volatiles were identified in the olives, from 7 chemical classes (alcohols, aldehydes, aromatic hydrocarbons, esters, ketones, sesquiterpenes, and terpenes). Generally, total volatile amounts decrease during maturation but toluene, the main compound, increased in all cultivars, particularly in those with higher susceptibility to olive fly. Sesquiterpenes also raised, mainly α-copaene. Toluene and α-copaene, recognized oviposition promoters to olive fly, were correlated with the infestation level of cvs. Madural and Verdeal Trasnmontana (intermediate and highly susceptible cultivars respectively), while no correlations were established with cv. Cobrançosa (less susceptible). No volatiles with inverse correlation were observed. Volatile composition of olives may be a decisive factor in the olive fly choice to oviposit and this could be the basis for the development of new control strategies for this pest.