http://www.skepticsannotatedbible.com/Luke Chapter 10, Jesus threatens a lot of random towns and cities with Divine Whacking:
Luke 10:13 Woe unto thee, Chorazin! woe unto thee, Bethsaida! for if the mighty works had been done in Tyre and Sidon, which have been done in you, they had a great while ago repented, sitting in sackcloth and ashes.
10:14 But it shall be more tolerable for Tyre and Sidon at the judgment, than for you.
10:15 And thou, Capernaum, which art exalted to heaven, shalt be thrust down to hell.These are most likely "retro-prophecies." Many of those are in the Old and New Testament--stuff obviously written years after the events, then back-fitted to appear like Amazing Predictions. (See also the Book Of Daniel.)
Some of the places mentioned were probably besieged--and/or flattened--by the Roman invasion of Judea in 66 CE. Vespasian and his son Titus met and combined their Legions at the coastal city of Ptolemais. Then they methodically moved inland, tightening the noose around Jerusalem by conquering the major cities of Galilee, Samaria, the Dead Sea region, and finally Judea.
Grumpy Atheist History Geek notes that Jebus was way late in uttering threats against the island fortress-city of Tyre. Alexander The Great had sacked the place 300 years before.
Luke 21: better not have any rug-rats around, especially young ones! Again, all this portentous croaking sounds like a story about the Roman attack on Jerusalem, retro-fitted much later and put in Jesus' mouth as a "prophecy:"
Luke 21:20 And when ye shall see Jerusalem compassed with armies, then know that the desolation thereof is nigh.
21:21 Then let them which are in Judaea flee to the mountains; and let them which are in the midst of it depart out; and let not them that are in the countries enter thereinto.
21:22 For these be the days of vengeance, that all things which are written may be fulfilled.
21:23 But woe unto them that are with child, and to them that give suck, in those days! for there shall be great distress in the land, and wrath upon this people.
21:24 And they shall fall by the edge of the sword, and shall be led away captive into all nations: and Jerusalem shall be trodden down of the Gentiles, until the times of the Gentiles be fulfilled.