Free flaps have become the preferred reconstructive approach to restore form and function for patients presenting with complex head and neck defects. For composite, complex defects for which a regular free flap might not meet all reconstructive demands, adequate coverage can be achieved with either a single chimeric free flap or a double free flap. We performed a single-center retrospective chart review of patients who underwent either single chimeric free flap or double free flap reconstruction. Indications for reconstruction included defects resultant from head and neck tumor or osteoradionecrosis resections. We extracted the following variables: tumor location, defect, flap(s) performed, and postoperative complications. Unpaired t-tests were performed to evaluate for statistically significant differences in complications encountered between the single chimeric versus the double free flap patient groups. In our series of 44 patients, a total of 55 single chimeric and double free flaps were performed. We found no significant difference in overall complications (p = 0.41) or flap/skin paddle loss (p = 0.45) between the groups. There were three total flap losses; two patients underwent successful salvage procedures and one patient died. The anterolateral thigh (ALT) was the most common free flap (70%) used in our series, and 98% of our patients completed successful reconstruction. As the initial reconstructive effort is critical for achieving favorable long-term outcomes in complex head and neck cases, effective and safe techniques should be employed to ensure optimal delivery of care. We believe that single chimeric and double free flap techniques should be appropriately utilized as part of the armamentarium of head and neck reconstructive microsurgeons.