Background/Objectives: Pediatric tracheotomy has evolved from an emergency procedure for acute infections to a planned intervention for chronic conditions requiring prolonged airway support. This study aims to describe the clinical characteristics, indications, and outcomes of pediatric tracheotomy over a 21-year period at a tertiary care center. Methods: A retrospective observational case series was conducted including 246 pediatric patients (0–18 years) who underwent tracheotomy between 2004 and 2024. Data were collected from medical records and included demographics, indications, procedural details, complications, decannulation, and mortality. Patients were categorized into airway obstruction (AO) and respiratory support (RS) groups. Statistical analyses were performed using the Mann–Whitney U test, Chi-square and Fisher’s exact test. Results: A significant increase in tracheotomy procedures was observed over time. Respiratory support was the predominant indication (75.2%), mainly due to neurological disorders, while airway obstruction accounted for 24.8%. Patients in the AO group were significantly younger and more likely to undergo urgent procedures (p < 0.001). Complication rates were comparable between groups (AO 16.4% vs. RS 21.1%; p = 0.295). Decannulation was significantly more successful in the AO group (16.4% vs. 5.4%; p = 0.012). Mortality did not differ significantly between groups and was associated with underlying comorbidities. Conclusions: Pediatric tracheotomy is increasingly performed for chronic respiratory support. While procedural safety is high, outcomes vary by indication, with better decannulation rates in airway obstruction cases. Multidisciplinary, individualized management is essential for optimizing patient outcomes.