Microwave technology plays a central role in current wireless communications, including mobile communication and local area networks. The microwave range shows relevant advantages with respect to other frequencies in open-air transmission, such as low absorption losses and low-energy consumption, and in addition, it is the natural working frequency in superconducting quantum technologies. Entanglement distribution between separate parties is at the core of secure quantum communications. Therefore, understanding its limitations in realistic open-air settings, especially in the rather unexplored microwave regime, is crucial for transforming microwave quantum communications into a mainstream technology. Here, we investigate the feasibility of an open-air entanglement distribution scheme with microwave two-mode squeezed states. First, we study the reach of direct entanglement transmission in open air, obtaining a maximum distance of approximately 500 m with parameters feasible for state-of-the-art experiments. Subsequently, we adapt entanglement distillation and entanglement swapping protocols to microwave technology in order to reduce the environment-induced entanglement degradation. The employed entanglement distillation helps to increase quantum correlations in the short-distance low-squeezing regime by up to 46%, and the reach of entanglement increases by 14% with entanglement swapping. Importantly, we compute the fidelity of a continuous-variable quantum teleportation protocol using open-air-distributed entanglement as a resource. Finally, we adapt this machinery to explore the limitations of quantum communication between satellites, where the impact of thermal noise is substantially reduced and diffraction losses are dominant.