Ouai can mean "woe," a word announcing doom, or "alas," meaning pity. Both ideas are appropriate here. Isaiah used the Hebrew equivalent22times. Chorazin stood about two miles northwest of Capernaum. This Bethsaida was probably the one on the northeast coast of the Sea of Galilee on the east side of the Jordan River (cf. Mark 6:45; Mark 8:22; Luke 9:10; John 1:44; John 12:21). Tyre and Sidon lay on the Mediterranean coast to the north. The Old Testament prophets often denounced Tyre and Sidon for their Baal worship. Sackcloth and ashes were common ancient Near Eastern accouterments to mourning. [source][source][source]
Jesus" statement reveals that as God He knew what the people of Tyre and Sidon would have done had they received the amount of witness the Jewish cities had enjoyed. It also indicates that the reception of special revelation is a privilege, not a right. Furthermore when God Judges , He will take into account the opportunity people have had. There are degrees of punishment in hell as there are degrees of felicity in heaven ( Matthew 11:41; Matthew 23:13; Luke 12:47-48; Romans 1:20 to Romans 2:16). [1][source]