The GH4169D superalloy, a novel Nickel-based material widely acknowledged for its exceptional high temperature strength and fatigue resistance properties, plays a pivotal role in the production of critical components of contemporary aero-engines. The material, however, falls under the category of a typical difficult-to-cut metallic material due to the substantial cutting forces and significant tool wear experienced during the machining process. In this paper, a method of longitudinal ultrasonic vibration assisted side milling (LUVM) was developed to extend tool life. The investigation primarily involved an analysis of tool wear behaviors, including milling force, tool life, morphologies of tool wear, and various underlying wear mechanisms in LUVM and conventional milling (CM) of GH4169D superalloy. The results demonstrate that LUVM exhibits the advantage of reducing milling forces and prolonging tool life in comparison to CM. Throughout the entire milling process, the maximum milling force of LUVM is consistently smaller than that of CM, displaying a comparatively slower growth trend. At the conclusion of machining, while CM reaches a maximum milling force of 360.3 N, the maximum milling force of LUVM (195.9 N) is significantly lower. The tool life of LUVM is 28.2 min, representing a 33 % increase compared to CM (21.2 min). Material adhesion, coating delamination, and built-up edge (BUE) phenomena can be observed on both the tool rake face and flank face in CM. LUVM contributes to mitigation of bonding phenomena, prevention of BUE formation, and avoidance of abrasive wear in comparison to CM. However, it is prone to lead to tool tip chipping. For CM, the tool wear mechanisms include adhesive wear, oxidation wear, abrasive wear and diffusion wear; whereas for LUVM, the tool wear mechanisms comprise of adhesive wear, oxidation wear and diffusion wear.