Column-to-column structural spans have been increasing in mid-rise and high-rise office buildings from 25 feet to 45-50 feet due to progress in artificial lighting technologies, structural systems, tenant pressures and zoning regulations. The length of free spans has a direct impact on the construction cost and a building’s sustainability, as longer spans require more structural materials to be built. The paper analyzes the relationship between column free spans and market performance (vacancy and rents) of tall office buildings while accounting for LEED certification and Energy Star label status. If evidence confirms that other building characteristics, including post construction sustainability adoption, has a higher impact on an office building marketability, new strategies can be initiated to reduce the structural spans of tall office buildings and therefore their embodied energy, without affecting their market value. The paper focuses on the class A office buildings of more than 600,000 square feet in downtown Chicago. The results suggest that buildings with shorter spans experience more vacancy, while rents do not have any statistically significant relationship with free spans. Additionally, higher LEED points are achieved by buildings with shorter spans.