Background/Objectives: Acute cholecystitis (AC) presents a significant burden in emergency surgical settings. Early laparoscopic cholecystectomy (ELC) is the standard of care for AC, yet its implementation varies. This study aims to assess the impact of preoperative waiting time (WT) on postoperative length of stay (LOS) in patients undergoing urgent cholecystectomy. Methods: From June 2021 to September 2022, data on patients undergoing urgent cholecystectomy for AC or pancreatitis were collected from two university hospitals. Patients were categorized into early (ELC) or delayed (DLC) cholecystectomy groups based on WT. The primary outcome was the assessment of the variables influencing LOS via univariate and multivariate analyses. Results: This study included 170 patients, predominantly female, with a median age of 64.50 years. ELC was performed in 58.2% of cases, with a median WT of 0 days, while DLC was performed in 41.8%, with a median WT of 3 days. Postoperative complications occurred in 21.8% of cases, with LOS being significantly shorter in the ELC group (median 5 days vs. 9 days; p = 0.001). Multivariate analysis confirmed that WT (OR 8.08 (1.65–77.18; p = 0.033)) was the most important predictor of LOS. Conclusions: ELC is associated with a shorter LOS and with DLC, aligning with the WSES recommendations. Earlier surgery reduces the risk of complications and overall hospital costs. An extended WT contributes to a prolonged LOS, underscoring the importance of timely access to operating theaters for acute biliary pathologies.