Aim: Head and neck region reconstructions are often delicate procedures that require different solutions at different layers. The use of chimeric flaps offers the interesting characteristic of combining different tissues, which is extremely valuable in this setting. In the present work, we share our experience with different types of conventional flaps, such as the radial flap, the medial sural artery perforator flap, and the fibula osteocutaneous flap. Methods: Over the last year, a series of five patients received advanced head and neck defects reconstruction employing chimeric flaps. The patients included two females and three males, with the mean age of 68-year-old. The defect was in four cases due to radical tumor resection in the oromandibular region. The fifth case was an osteoradionecrosis which needed a complete resection of the affected soft and bony tissue. Results: All five patients were successfully treated. Two of them received a chimeric free flap composed of multiple skin islands while the other three also comprised bone tissue transfer for mandible reconstruction. The mean follow-up period was ten months (range 3-8 months), and during this period neither postoperative complications nor signs of disease relapse were noted. Conclusion: The results obtained resorting to the chimeric fashion of various free flaps suggests that they are an excellent solution from both the functional and aesthetic point of view. Specific technical modifications are proposed according to the case requirements.