Jerusalem
The only city which God Himself “lamented” over directly as He says:
“Jerusalem, Jerusalem, who kills the prophets and stones those who are sent to her! How often I wanted to gather your children together, the way a hen gathers her chicks under her wings, and you were unwilling.
Behold, your house is being left to you desolate!
For I say to you, from now on you will not see Me until you say, ‘BLESSED IS HE WHO COMES IN THE NAME OF THE LORD!’” – Lord Jesus Christ (Matthew 23:37 – 39)