Pray that your flight will not take place in winter or on the Sabbath.
To what does this refer - why the concern about flight on the Sabbath?
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The notes on Matthew 24:20 in the NIV Study Bible say:
"or on the Sabbath - Matthew alone includes this because he was writing to Jews, who were forbidden to travel more than about half a mile om the Sabbath."
However, there does not seem to be any such written law in the Law of Moses, so perhaps this was a later interpretation. Matthew Henry's Commentary gives this further point, worth noting. He says that Jesus' words intimate that
"...the sabbath is ordinarily to be observed as a day of rest from travel and worldly labour, but that according to his own explication of the fourth commandment, works of necessity were lawful on the sabbath day, as this of fleeing from an enemy to save our lives. Had it not been lawful, he would have said, 'Whatever becomes of you, do not flee on the sabbath day, but abide by it, though you die by it'." [page 1385, middle column]
Given that Jesus did not say any such thing, but commanded his followers to flee for their very lives when that deadly attack took place, he clearly knew that the circumstances would be so dire, that nothing less than urgent, immediate flight to safety would save their lives. There may be some similarity with the warning given in the last book of the Bible, the Revelation, about fleeing from Babylon the Great, before God's sudden and dreadful destruction falls on it. All those who don't make haste to flee before then, will suffer her plagues. Likewise, with what Jesus said here - all those who did not take on board the immense gravity of what he was warning them of, would lose their lives, so they had to be prepared to flee, even on the sabbath day, but his Jewish audience would prefer flight on any day other than the sabbath. Not that they would be given a choice, but praying earnestly about that could, in the grace of God, make a difference.
This is part of the discourse on impending destruction. Some read this chapter as a reference strictly to the events of the Roman-Jewish war of 66-73; others read it as a prophetic statement referring to two future events--the Roman-Jewish war and a subsequent second coming of Christ.
(For a discussion of the prevalence of dual fulfillment prophecies in Jewish literature, see Victor Ludlow Isaiah: Prophet, Seer, and Poet pp. 53-54)
John AT Robinson--who suggests this is not a "prophecy" made after the fact--points out multiple instances where the apocalyptic language in this chapter and the parallel passages is inspired by 1 Maccabees. He made the following observations about the "flight on the Sabbath":
The reference to the sabbath could again contain an allusion back to the fact that when the faithful of Judaea took to the hills after the original 'abomination of desolation' their first encounter with the enemy was on the sabbath and because of scruples which they later abandoned they were massacred without resistance (I Mace. 2.29-41)
But it is more likely to refer to the obstacles to movement on the sabbath for Jewish Christians who were strict observers of the law (see here p. 23)
This latter point is a reference to the oral traditions among some Jews limiting the number of steps that could be taken on the Sabbath (see here).
Fleeing on the Sabbath could be seen as a bad thing either because of its disastrous consequences for the Maccabean revolt a century and a half prior, or because of oral traditions regarding travel on the Sabbath.
The OP focuses on the "sabbath" portion of the verse rather than "winter". Two points that may be of interest relative to flight in winter: