The trachea has a complex anatomy to fulfill its tasks. Its unique fibro-cartilaginous structure maintains an open conduit during respiration, and provides vertical elasticity for deglutition, mobility of the neck and speech. Blood vessels pierce the intercartilaginous ligaments to perfuse the ciliated epithelium, which ensures effective mucociliary clearance. Removal of a tracheal segment affected by benign or malignant disease requires airtight restoration of the continuity of the tube. When direct approximation of both tracheal ends is no longer feasible, a reconstruction is needed. This may occur in recurrent short-segment defects in a scarred environment, or in defects comprising more than half the length of the trachea. The resulting gap must be filled with vascularized tissue that restores the mucosal lining and supports the semi-rigid, semi-flexible framework of the trachea. For long-segment or circular defects, restoration of this unique biomechanical profile becomes even more important. Due to the inherent difficulty of creating such a tube, a tracheostomy or palliative stenting are often preferred over permanent reconstruction. To significantly improve and sustain quality of life of these patients, surgeons proposed innovative strategies for complex tracheal repair. In this review, we provide an overview of current clinical applications of tracheal repair using autologous and allogenic tissues. We look at recent advances in the field of tissue engineering, and the areas for improvement of these first human applications. Lastly, we highlight the focus of our research, in an effort to contribute to the development of optimized tracheal reconstructive techniques.