Local and global π-electron delocalization occurring in planar poly-1,7-[N]calicenes is investigated with use of 10 aromaticity measures based on different physical properties. Systematic change of aromatic character is observed along chains of connected calicene units. Multidimensionality of the aromaticity phenomenon is studied with use of principal component analysis (PCA). The structural characteristics are compared with the properties of the isolated calicene molecule exposed to external electric fields of various intensities. Interrelations between the value of electric field applied and physical properties of the calicene molecule are discussed in the context of calicene unit affected by its surroundings in polycalicene chains. The patterns of global π-electron delocalization are described in graph theory terminology, and interconnections between local and global aromaticity in these systems are established.