Reconstruction of head and neck defects following oncological ablative surgery represents a considerable challenge for reconstructive surgeons. Common reconstruction options are the fibula, iliac crest, tip scapular and lateral scapula border free flap. The vascularized iliac crest free flap was first described by Taylor et al. in 1979 and it has been widely used for the reconstruction of composite head and neck defects. This flap guarantees excellent functional and aesthetic outcomes in the reconstruction of posterior segmental mandible defects. For the reconstruction of maxillary defects, it is important to note that the iliac crest bone shape usually allows for an adequate reconstruction without the need to conduct any osteotomies, and this substantially facilitates the flap inset. Thus, the iliac crest free flap offers a valuable reconstructive alternative that should be part of the armamentarium of all head and neck reconstructive surgeons. When this option is well indicated, the success rate, as well as functional and aesthetic outcomes, are comparable to other flaps used for reconstructing the maxillofacial area. The main aim of the present report is to analyze the importance of the DCIA flap for the reconstruction of complex defects of the maxillofacial region and to present possible applications, suggestions, and pitfalls associated with this technique.