Climate-related extended outbreaks and range shifts of destructive bark beetle species pose a serious threat to urban boreal forests in North America and Fennoscandia. Recent developments in low-cost remote sensing technologies offer an attractive means for early detection and management of environmental change. They are of great interest to the actors responsible for monitoring and managing forest health. The objective of this investigation was to develop, assess, and compare automated remote sensing procedures based on novel, low-cost hyperspectral imaging technology for the identification of bark beetle infestations at the individual tree level in urban forests. A hyperspectral camera based on a tunable Fabry-Pérot interferometer was operated from a small, unmanned airborne vehicle (UAV) platform and a small Cessna-type aircraft platform. This study compared aspects of using UAV datasets with a spatial extent of a few hectares (ha) and a ground sample distance (GSD) of 10–12 cm to the aircraft data covering areas of several km2 and having a GSD of 50 cm. An empirical assessment of the automated identification of mature Norway spruce (Picea abies L. Karst.) trees suffering from infestation (representing different colonization phases) by the European spruce bark beetle (Ips typographus L.) was carried out in the urban forests of Lahti, a city in southern Finland. Individual spruces were classified as healthy, infested, or dead. For the entire test area, the best aircraft data results for overall accuracy were 79% (Cohen’s kappa: 0.54) when using three crown color classes (green as healthy, yellow as infested, and gray as dead). For two color classes (healthy, dead) in the same area, the best overall accuracy was 93% (kappa: 0.77). The finer resolution UAV dataset provided better results, with an overall accuracy of 81% (kappa: 0.70), compared to the aircraft results of 73% (kappa: 0.56) in a smaller sub-area. The results showed that novel, low-cost remote sensing technologies based on individual tree analysis and calibrated remote sensing imagery offer great potential for affordable and timely assessments of the health condition of vulnerable urban forests.