Heavy-duty freight transport remains one of the most difficult sectors to decarbonize due to its high energy demand, long-distance operation, and strong dependence on diesel fuel. In Chile, more than 90% of heavy trucks operate with diesel engines, contributing significantly to greenhouse gas emissions and local air pollutants. At the same time, Chile has favorable conditions for the development of green hydrogen due to its world-class solar and wind resources. This study presents a technical and economic assessment of green hydrogen fuel cell trucks recently introduced in Chile, comparing their operational performance with conventional diesel freight trucks. A techno-economic framework based on total cost of ownership, fuel consumption, operational range, fleet utilization, and hydrogen price scenarios was developed using information reported in public studies and official Chilean strategic documents. The results indicate that hydrogen trucks are technically suitable for long-haul and intensive-duty operations due to their rapid refueling capability and high operational autonomy. However, economic competitiveness remains strongly dependent on hydrogen price, fleet scale, infrastructure utilization, and vehicle capital cost. Under current market conditions, diesel trucks preserve cost advantages, while hydrogen trucks become increasingly competitive as hydrogen prices approach long-term target values and annual mileage increases. Chile’s renewable resource base positions the country as a strategic candidate for early adoption in mining, logistics corridors, and captive fleets. The study concludes that hydrogen freight transport can become a realistic decarbonization pathway if accompanied by targeted public policies, infrastructure deployment, and industrial scale-up.