Open and cyclic chains from two to eight units of ICl and IF are constructed and examined by density functional theory (DFT) calculations. These chains contain either I•••I or I•••X halogen bonds (XBs) where X refers to Cl or F. The closed rings are more stable than the open chains due to the presence of an additional XB and enhanced cooperativity. This pattern is true even for most trimers where there is sizable geometric distortion in the rings. I•••F rings are generally more stable than the corresponding I•••I cycles as the I•••F bond is stronger than I•••I even in the simple dimer. However, I•••I rings are comparable in energy to I•••Cl. It is possible to construct I•••I rings of at least as large as eight units, which are held together exclusively by XBs. On the other hand, the maximum possible size of I•••X rings is 6. Red shifts are observed in the I−X stretching frequency bands, which magnify as the chain, both cyclic and open, grows longer. The NMR chemical shielding of the I atoms increases for I•••I chains but diminishes when I•••Cl bonds are present.