A combination of Nobel macrocycle-crown ether and star macrocycle-pillararenes together in organic synthesis and material science is significant in obtaining hybrid systems, with rigid/flexible structural architecture, induced planar chirality, a negative cooperative effect and multiple fused cyclic hosts. In this review, we will discuss the synthesis/preparation of crown ether-pillararene hybrid macrocyclic systems by covalent bonds, supramolecular interactions and mechanical bonds, leading to hybrid compounds, supramolecular assemblies and mechanically interlocked molecules. The practical applications of crown ether-containing pillararenes will also be discussed in diverse areas, such as molecular recognition via fused multiple macrocycles and ion channels as well as external stimuli-responsive smart materials. We also call the attention of related researchers towards academic and technical issues about topological structures and applied functions in this fresh new fused macrocyclic field.