Improving fuel efficiency in freight transport is crucial for reducing both operational costs and environmental impact. This paper presents a dual-method approach to evaluating aerodynamic technologies for heavy-duty trucks in Chile, combining field experimentation with the foundation for future simulation-based methodologies. Two experimental trials were conducted: the first assessed the impact of aftermarket aerodynamic kits, and the second compared fuel consumption between cab-over-engine (COE) and conventional cab configurations, using a standardized national testing protocol (NCh3331). Results showed that aerodynamic kits can reduce fuel consumption by up to 15.4%, while cab design alone can yield an efficiency gain of 3.96%. These findings highlight the potential of simple design optimizations to yield substantial economic and environmental benefits, with CO2 reductions reaching 479,500 kg annually under full fleet implementation. However, implementation in Chile remains low due to regulatory constraints, limited commercial availability, and a lack of localized performance data. To address this, we propose the development of a data-driven simulation model calibrated with real-world telemetry and GPS data, enhancing the replicability and scalability of results across diverse operating conditions. This research highlights the significance of local technological validation and intelligent transportation modeling in bridging the gap between international innovations and regional applicability. The findings support regulatory reform and targeted deployment of aerodynamic solutions, contributing to Chile’s national sustainability and transport efficiency goals.