The study investigates the impact of a bridge connecting high-rise buildings on their stress–strain state (SSS) under wind loads. The relevance of the research is determined by the widespread use of ‘skybridges’ in modern megacities. The methodology is based on numerical modeling of various configurations of the complex: with different building height ratios (1:1 and 1:0.6) and different vertical positions of the bridge. Criteria for evaluating the SSS of buildings were defined: natural frequencies, forces in the ground-floor columns, and displacements of the upper floors. Calculations were performed using the SOFiSTiK software package, including analyses with geometric nonlinearity. The results showed that the presence of a rigidly fixed bridge significantly affects the redistribution of internal forces and the stiffness of the system. The most effective solution is achieved when the rigidly fixed bridge is located at the level of the upper floors, which reduces horizontal displacements by up to 67%.