Pray that your flight may not be in winter or on a SABBATH

Gabriel prophesied to Daniel in 9:

27 "He will confirm a covenant with many for one week, but in the middle of the week he will put an end to sacrifice and offering. And on the wing of the temple will come the abomination that causes desolation, until the decreed destruction is poured out upon him."

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A certain man dressed in linen (Da 10:4) prophesied to Daniel in 11:

31 His forces will rise up and desecrate the temple fortress. They will abolish the daily sacrifice and set up the abomination of desolation.

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This was fulfilled at least partially in 167 BCE. Antiochus IV Epiphanes, a Seleucid king persecuted the Jewish people and desecrated the Second Temple in Jerusalem. He ordered the cessation of the daily sacrifices and erected an altar to Zeus in the Temple, where he also sacrificed pigs, an unclean animal according to Jewish law. This act of desecration was seen as the "abomination that causes desolation".

Before Jesus was born, Herod rebuilt the temple.

Lk 21:

20 “But when you see Jerusalem surrounded by armies, then know that its desolation has come near. 21 Then let those who are in Judea flee to the mountains, and let those who are inside the city depart, and let not those who are out in the country enter it, 22 for these are days of vengeance, to fulfill all that is written. 23 Alas for women who are pregnant and for those who are nursing infants in those days! For there will be great distress upon the earth and wrath against this people. 24 They will fall by the edge of the sword and be led captive among all nations, and Jerusalem will be trampled underfoot by the Gentiles, until the times of the Gentiles are fulfilled.

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Parallel account, Mt 24:

1 Jesus left the temple and was going away, when his disciples came to point out to him the buildings of the temple. 2 But he answered them, “You see all these, do you not? Truly, I say to you, there will not be left here one stone upon another that will not be thrown down.”

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Jesus foretold the temple destruction in 70 CE.

3 As he sat on the Mount of Olives, the disciples came to him privately, saying, “Tell us, when will these things be, and what will be the sign of your coming and of the end of the age?”

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The start of the Olivet discourse.

15 “So when you see the abomination of desolation spoken of by the prophet Daniel, standing in the holy place (let the reader understand),

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There would be more fulfillment to Daniel's prophecy on the abomination of desolation in the context of a future temple destruction. To simplify the wording for the Gentile readers, the parallel account in Luke did not use the phrase "abomination of desolation spoken of by the prophet Daniel".

In 70 CE, Roman soldiers brought their military standards, which bore images of the emperor and Roman eagles into the Temple. Eagles were unclean birds. They offered sacrifices to these images at the temple's ruined eastern gate.

16 then let those who are in Judea flee to the mountains. 17 Let the one who is on the housetop not go down to take what is in his house, 18 and let the one who is in the field not turn back to take his cloak.

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Flee quickly while you can.

19 And alas for women who are pregnant and for those who are nursing infants in those days!

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It would be more difficult for these women to flee. All three accounts (Mk 13:17, Mt 24:19, Lk 21:23) mentioned "pregnant" and "nursing".

20 Pray that your flight may not be in winter or on a Sabbath.

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Winter would make fleeing more difficult for everyone. Mk 13:18 and Mt 24:20 mentioned "winter" but Luke didn't.

For the religious, they would need to flee on a Sabbath. Jewish religious laws restricted travel distance on the Sabbath. Again, to simplify it for the Gentiles, Luke didn't mention "Sabbath" in his parallel account. Neither did Mark.

Rome laid siege to Jerusalem and destroyed it in the summer. Babylonians destroyed the First Temple on the 9th of Aviv. Rome destroyed the Second Temple on the same date. It was a Sabbath day.

So far, the words of Jesus were fulfilled by the destruction of the Second Temple, at least partially. But he continued:

21 For then there will be great tribulation, such as has not been from the beginning of the world until now, no, and never will be.

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Matthew presented the "Great Tribulation" as one of a kind. Mark 13:19 called it "such tribulation". Luke 21:23 again simplified the concept as "great distress", not necessarily one of a kind.

24 “But in those days, after that tribulation, the sun will be darkened, and the moon will not give its light, 25 and the stars will be falling from heaven, and the powers in the heavens will be shaken. 26 And then they will see the Son of Man coming in clouds with great power and glory. 27 And then he will send out the angels and gather his elect from the four winds, from the ends of the earth to the ends of heaven.

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All three accounts mentioned the coming of the Son of Man.

Will the Third Temple be built?

Perhaps.

Will there be a future Great Tribulation?

I think so. There will be a complete and ultimate fulfillment of Jesus' words here.

Will people worry about it happening on the Sabbath?

Mark and Luke didn't mention the Sabbath. Only Matthew did. When it happens, maybe some religious Jews and Christians would worry about it. I wouldn't.

Jesus said, "Pray that your flight may not be in winter or on a Sabbath." Does that mean that Christians should observe the Sabbath?

No, that would be an overgeneralization to conclude that. Matthew addressed that concern to the Jews living in Jerusalem. Luke's target audience was the Gentile. He didn't bother to mention that particular concern. I'm a bit surprised that even Mark didn't mention it.

Do I imply that Christians should not observe the weekly Sabbaths?

No. That would be another over-generalization. I try not to over-generalize one way or another.