Who were Lavan's "brothers" that he took with him to chase Yaakov?
Rashi: They were his relatives. 1
Ramban: He took every mighty man from Charan.
Tosfos ha'Shalem (to 31:25 (3), citing a Midrash): They were dogs. 2
Ramban (to 31:46): They were also Yaakov's relatives, for they are from Nachor's family. (The Pasuk there connotes that they are Yaakov's brothers.) He did not want to confront Yaakov with strangers, who would indulge in quarrels with Yaakov and even steal from him.
This best explains "Taka Es Echav" (31:25) (PF).
How far apart was Lavan from Yaakov when he (Lavan) set out to catch up with him? When did he catch up?
Rashi: Lavan had left town, where they both lived, 1 to shear his sheep (which were three days away). When Yaakov left town, it took three days for Lavan's men to inform him of the new developments. Meanwhile Yaakov fled in the opposite direction, in which case Lavan was six days away from Yaakov - and, as the Pasuk relates, he caught him up on the next day. 2
Riva, citing Chizkuni: Lavan returned to Charan (on day three), delayed three days (and gathered his "brothers;" refer to 31:23:1:2), and from there went seven days' journey on the seventh day. We must say that even Lavan 4 rested on Shabbos. 5
Bechor Shor: Lavan traveled in four days (days four through seven) what Yaakov traveled in seven days. 6
See Ba'alei Tosfos (Hadar Zekenim).
See also Rashbam.
He comes to explain why Rashi says that Lavan went in one day what Yaakov went in seven. If Lavan was to the east of Charan, and Yaakov went west (towards Eretz Yisrael), he was more than seven days' journey away! Perhaps he returned to Charan on the sixth day, looked for his Terafim and gathered his "brothers," and from there went seven days' journey on the seventh day. Or, Lavan was roughly north or south of Charan, and Yaakov was six days from him, and six days from Charan. Lavan went directly after Yaakov (he knew that he was going to Eretz Kena'an). His brothers were already with him (refer to 31:19:151:1), and the informer had looked for the Terafim, and told Lavan that they were missing. (PF)
Perhaps [even] Yaakov went on Shabbos. There was concern for Piku'ach Nefesh (lest Lavan chase him to kill him), and outside of Eretz Yisrael he would transgress Torah law when needed (refer to 29:28:151:4 - PF)!
Riva rejects this. Surely Lavan ha'Rasha did not observe Shabbos! Rather, Rashi means that Lavan traveled in one day (day four) what was seven days' journey for Yaakov. Also the Rosh and Hadar Zekenim explain like this.
It seems that the four days are from when Lavan was told. Why does the calculation exclude Lavan's return to his house to find that his Terafim were taken? Perhaps the informer went to ask the Terafim, found that they are gone, and Lavan trusted him and immediately went east to pursue Yaakov. If Lavan was roughly north or south of Charan, we can say that seven days east of Charan was also seven days away from Lavan. This Perush connotes that Yaakov went also on Shabbos. Refer to 31:23:2:3*. (PF)
What was special about Har ha'Gil'ad?
Malbim: There, Lavan recognized Yaakov's path, that he was heading for Har ha'Gil'ad. Until now, he did not know the path Yaakov had taken.
Ha'amek Davar: Yaakov realized that he cannot push the children and flock to flee more (without resting), so he went off the road to rest in Har ha'Gil'ad, which is good pasture, and Lavan caught him there.
Why did Yaakov not have Kefitzas ha'Derech?
Ohr ha'Chayim #1: Hashem wanted to show him that he did not need to flee. Even though Lavan caught him, he could not even speak to [harm] him. This was a bigger miracle, to show that Hashem will stop one with choice from harming Yaakov.
Ohr ha'Chayim #2: Hashem caused that they make a Bris not to harm each other. Through this, Yisrael overpowered in the days of Kushan Rish'asayim (Sanhedrin 105a), and Rachel died on the way, 1 for the benefit of her children when they went to exile.
Through Yaakov's words ,"Im Asher Timtza Es Elohecha Lo Yichyeh" (31:32). Even without this, could Rachel not die on the way for her own words "Mesah Anochi" (30:1), or for selling a night's intimacy with Yaakov, or for speaking up before her older sister? Four people died [solely] due to the sin [of Adam and Chavah, which came via] the snake (Shabbos 55b)! (PF)
QUESTIONS ON RASHI
Rashi writes: "'A seven days' journey' - All three days that the informer went towards Lavan, Yaakov progressed on his way; such that [when he heard,] Lavan was six days' journey away." Why does Rashi assume that Lavan was in the polar-opposite direction (e.g. Lavan went north, while Yaakov was traveling south)? Perhaps Lavan had gone east or west, and he was closer (about 4 days)?
Gur Aryeh #1: The verse tells us that Lavan brought his kinsmen along in the chase. He must have returned home to gather them. 1
Gur Aryeh #2: The verse specifies that Lavan heard of Yaakov's departure only on the third day. Only if it means that Yaakov was escaping in the exact opposite direction, does the Pasuk clarify for us what the distance was between Lavan and Yaakov. 2
Meaning, irrespective of where Lavan was now located, he could not pursue Yaakov by the shortest route; he needed to cover the three days' journey home first. Additionally, Lavan must have returned home, for how else would he know that his Terafim had been stolen? (CS)
As a rule, when the Torah specifies details, it comes to clarify matters for us, not to make them more ambiguous. Here it clarifies that Lavan was the maximum distance away from Yaakov. (EK)
Rashi writes: "And Lavan caught up on the seventh [day]." But only four days had elapsed?
Gur Aryeh: Rashi means only that Lavan had been seven days' journey away, but now he caught up.