Actually, the 69 weeks already took place at the time Jesus came the first time.
Daniel the prophet said: "So you are to know and understand that from the issuing of a decree to restore and rebuild Jerusalem, until Messiah the Prince, there will be seven weeks and sixty-two weeks; it will be built again, with streets and moat, even in times of distress. Then after the sixty-two weeks, the Messiah will be cut off and have nothing, and the people of the prince who is to come will destroy the city and the sanctuary." (Daniel 9:25-26)
So from the issuing of the decree to restore and rebuild Jerusalem until Messiah comes and is cut off, there was exactly 69 weeks (7 weeks + 62 weeks). (In Bible prophecy a week is 7 years.) The 7 weeks or 49 years are the time it took to rebuild Jerusalem with streets and moat. Then we count off 62 weeks after that. Jesus was crucified or cut off after a total of 69 weeks (or 483 years).
We can see this from history.
King Artaxerxes of Persia gave a decree around 445 BC to restore and rebuild Jerusalem.
“And it came about in the month Nisan, in the twentieth year of King Artaxerxes” (Nehemiah 2:1), Nehemiah was allowed to go to Jerusalem to rebuild it.
“And I [Nehemiah] said to the king, ‘If it please the king, let letters be given me for the governors of the provinces beyond the River, that they may allow me to pass through until I come to Judah, and a letter to Asaph the keeper of the king’s forest, that he may give me timber to make beams for the gates of the fortress which is by the temple, for the wall of the city and for the house to which I will go.’ And the king granted them to me because the good hand of my God was on me.” (Nehemiah 2:7-8)
This was around 445 BC. After 7 weeks (49 years), Jerusalem was rebuilt in 396 BC. After this, 62 weeks or 434 years passed. We land in around 32 AD when Jesus the Messiah was crucified.
(Note: According to Daniel, a year was 360 days, which was Jewish prophets’ tradition for calculations. So with this calculation, we land around 32 AD in the Julian calendar when Jesus was crucified.)
In 70 AD, during the Jewish-Roman War, Jerusalem was breached by the Romans and the temple in Jerusalem was destroyed.
Thus, the prophecy of Daniel regarding the 7 weeks + 62 weeks was fully fulfilled: “Then after the sixty-two weeks, the Messiah will be cut off and have nothing, and the people of the prince who is to come will destroy the city and the sanctuary” (Daniel 9:26).
So after the 69 weeks, Jesus was crucified and later on Jerusalem was destroyed.
Then we have a floating week that can start at any time. This is the 7 years of Tribulation that Daniel also spoke of.
“…Even to the end there will be war; desolations are determined. And he will make a firm covenant with the many for one week, but in the middle of the week he will put a stop to sacrifice and grain offering; and on the wing of abominations will come one who makes desolate, even until a complete destruction, one that is decreed, is poured out on the one who makes desolate.” (Daniel 9:26-27)
This floating week is the Tribulation that starts when the Antichrist makes a covenant with many peoples for one week (or 7 years). This is a week that can happen at any time during the current church age, because this week directly follows the rapture.
Jesus said no one knows at what time He will come to take His followers (rapture).
"But of that day and hour no one knows, not even the angels of heaven, nor the Son, but the Father alone. For the coming of the Son of Man will be just like the days of Noah. For as in those days before the flood they were eating and drinking, marrying and giving in marriage, until the day that Noah entered the ark, and they did not understand until the flood came and took them all away; so will the coming of the Son of Man be." (Matthew 24:36-39)
So Jesus can come and gather His people at any time to save them from the Tribulation. After He gathers His own in the rapture, the Antichrist will come and rule for one week (7 years). The reason the last week is floating is because no one knows when Jesus will come to start this clock.
There are no conditions that need to be met for Jesus to come to rapture His followers. That's why we need to be prepared for Jesus' coming, because He can come at any time.
For the nation of Israel, during the worst time of the Tribulation, they will get a chance to flee into the wilderness (Revelation 12:6, 13-14).
“Now at that time Michael, the great prince who stands guard over the sons of your people, will arise. And there will be a time of distress such as never occurred since there was a nation until that time; and at that time your people, everyone who is found written in the book, will be rescued.” (Daniel 12:1)
In the wilderness, God will teach the Jewish people like He did during the time of Moses.
“‘…I will bring you into the wilderness of the peoples, and there I will enter into judgment with you face to face. As I entered into judgment with your fathers in the wilderness of the land of Egypt, so I will enter into judgment with you,’ declares the Lord God. ‘I will make you pass under the rod, and I will bring you into the bond of the covenant; and I will purge from you the rebels and those who transgress against Me…'” (Ezekiel 20:36-38)
Then as a nation, the Jewish people will know Jesus is the Messiah and accept the new covenant.
Jesus gave a hint to the nation of Israel: “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!’” (Matthew 23:39).
The apostle Paul said:
“Now if their transgression is riches for the world and their failure is riches for the Gentiles, how much more will their fulfillment be! … For if their rejection is the reconciliation of the world, what will their acceptance be but life from the dead?” (Romans 11:12,15)
In the end, all the remnant of Israel will be saved (Romans 11:26). When Israel believes, Christ the Messiah will start His reign on earth!
So while there are no conditions to be met for Jesus to come for the rapture, after the rapture of Jesus' disciples, all the rest of these events will take place. Israel as a nation will believe and be saved. After this, Jesus will come to earth to reign.