The importance of transport infrastructure for individual well-being and regional economic development and growth, but also its adverse side-effects, make a comprehensive assessment of the general appropriateness of new construction and rebuild indispensable. Assessments, however, often lack certain issues. For instance, aesthetic aspects are usually not part of the (economic) evaluation of large infrastructure projects, albeit individuals may be (positively or negatively) affected by the aesthetic ‘value’ of infrastructures. This paper proposes the aesthetic index developed by Birkhoff as a method to quantify the aesthetic impact of buildings/facilities in urban areas. To test the basic applicability of the index for transport infrastructure facilities, we apply it at first to airport terminals in Germany. We also test the suitability of the index to derive the willingness to pay for aesthetic exterior design—since market prices are easy to obtain with respect to hotel room rates—using hotel architecture as the first example. Regression results of a hedonic price model indicate a significant relationship, suggesting the basic suitability of the index to uncover consumers’ willingness to pay for an aesthetic outward appearance. We suggest further research to test the suitability of Birkhoff’s index for general urban transport infrastructures in order to derive utility-based welfare measures toward aesthetic issues. For highly controversial urban (overground) infrastructures, we propose the inclusion of an aesthetic component in cost–benefit analysis.