[Mat 24:20 NASB] 20 "But pray that your flight will not be in the winter, or on a Sabbath.
With the holidays around the corner many of us are travelling to be with family and friends, and many travel by air. Travel is often difficult, especially in the winter because of cancellations and what not. And the Sabbath is especially busy. Oh, and having a nursing baby - everything is overwhelming. (Personally, from Thanksgiving to New Years I stay home because a lot of "turkeys" get killed during the holidays)!
So it is easy to appreciate that during the great tribulation one would pray that they don't have to go through Detroit airport in winter!
But Jesus suggests that flight from the great tribulation in winter will not just be inconvenient but problematic such as the Jews had ever experienced or ever would:
[Mat 24:19-21 NASB] 19 "But woe to those who are pregnant and to those who are nursing babies in those days! 20 "But pray that your flight will not be in the winter, or on a Sabbath. 21 "For then there will be a great tribulation, such as has not occurred since the beginning of the world until now, nor ever will.
Now we know that Haman's attept to annihilate the Jews was a dark day and the Shoah/Holocaust was a day of deep darkness for the Jews however, the "flight" of the elect Jews from Judea into the mountains to hide in caves is said to be even more catastrophic than these events.
So when is this horrific flight to take place? Or has it already?
[Jer 30:3, 5, 7, 11, 18 KJV] 3 For, lo, the days come, saith the LORD, that I will bring again the captivity of my people Israel and Judah, saith the LORD: and I will cause them to return to the land that I gave to their fathers, and they shall possess it. ... 5 For thus saith the LORD; We have heard a voice of trembling, of fear, and not of peace. ... 7 Alas! for that day [is] great, so that none [is] like it: it [is] even the time of Jacob's trouble; but he shall be saved out of it. ... 11 For I [am] with thee, saith the LORD, to save thee: though I make a full end of all nations whither I have scattered thee, yet will I not make a full end of thee: but I will correct thee in measure, and will not leave thee altogether unpunished. ... 18 Thus saith the LORD; Behold, I will bring again the captivity of Jacob's tents, and have mercy on his dwellingplaces; and the city shall be builded upon her own heap, and the palace shall remain after the manner thereof.
[Exo 10:14 NIV] 14 they invaded all Egypt and settled down in every area of the country in great numbers. Never before had there been such a plague of locusts, nor will there ever be again.
See also: https://judaism.stackexchange.com/questions/88491/is-the-fall-of-babylon-considered-to-be-israels-darkest-day