I would presume that Pyridinium Chlorochromate is not organic soluble due to the relatively strong ionic bonding between the anion and cation on account of their similarly large size. Although the charge on the pyridine is not stabilised by resonance, the charge on the chromium molecule is. Does this weaken the ionic bond enough so that the weak London forces between organic solvent molecules and the ions is enough to pull them apart? Are there other factors at play here?
Apart from the fact noted by Mithoron that it's soluble in polar organic solvents, we may consider what lattice binding energy the solvation forces must overcome. In a compound like sodium chloride with compact, monatomic ions the lattice forces are too strong for all but the most aggressive solvents (but lithium salts have a way around this problem). With pyridinium chlorochromate (PCC), however, the ions are multiatomic, bulky, and differently shaped as well as having only one charge, so the crystal lattice is only weakly bound compared with sodium chloride. PCC is far from unique; to cite another example, the triangular cyclopropenyl cation was identified through its nmr specta when salts were dissolved in polar solvents.