Matthew 16:1 Then the Pharisees and Sadducees came, and testing Him asked that He would show them a sign from heaven. 2 He answered and said to them, “When it is evening you say, ‘It will be fair weather, for the sky is red’; 3 and in the morning, ‘It will be foul weather today, for the sky is red and threatening.’ Hypocrites! You know how to discern the face of the sky, but you cannot discern the signs of the times. 4 A wicked and adulterous generation seeks after a sign, and no sign shall be given to it except the sign of the prophet Jonah.” And He left them and departed.
the signs of the times
A wicked and adulterous generation seeks after a sign, and no sign shall be given to it except the sign of the prophet Jonah.
So what's the sign of the prophet Jonah?
2 Kings 14:25 He restored the border of Israel from the entrance of Hamath as far as the Sea of the Arabah, according to the word of the LORD, the God of Israel, which He spoke through His servant Jonah the son of Amittai, the prophet, who was of Gath-hepher.
The restored borders of Israel
Now a question...
You might think that (A wicked and adulterous generation,) the adulterous would be included in the wicked category, not so. The adulterous are affiliated with Jezebel, spiritual adultery.
a sign of the times
I’m no expert, but I believe the “sign of Jonah” that He was referring to was that Jonah was in the belly of the fish for 3 days/nights and that was a foreshadowing of His death and ressurection. Not a prediction of the restoration of the modern day Israel’s borders.