When did this occur?
Rashi: It was when Yehoram was ill in Yizre'el.
Whom did he tell to do so?
Rashi (from Seder Olam 18): It was Yonah ban Amitai.
What is the meaning of "gird your loins"?
Rashi: This is an expression of acting with zeal and Gevurah, for he was sent on a dangerous mission.
Radak: He should go quickly and return quickly, while Yehoram is not here; he was recovering in Yizre'el. It says "v'Nastah v'Lo Sechakeh" (verse 3).
Malbim: Run quickly, for now it is easy to seize power. Yehoram was ill in Yizre'el with no one to help him, for all of [the army of] Yisrael were in Ramos Gil'ad.
Why should he take oil? We do not anoint Malchei Yisrael with oil!
Radak (citing Horiyos 11b): It was due to the opposition of Yehoram ben Achav. He did not take Shemen ha'Mishchah; that is only for Malchei Beis David. Rather, it was Afarsimon oil. Malbim (2) - he wanted it to resemble anointment with Shemen ha'Mishchah.
What is the significance of anointing him from a flask?
Radak citing Megilah 14a: David and Shlomo were anointed with a horn 1 (of oil), and their kingships lasted. Sha'ul and Yehu were anointed with flasks, and their kingships did not last.
Megilah 14a: "Ramah Karni" (Shmuel I, 2:1) - my horn is raised, but not my flask.
Hashem commanded Eliyahu to anoint Chaza'el, Yehu and Elisha. Why did Elisha appoint Chaza'el, and command to anoint Yehu?
Malbim: Elisha's request "vi'Yhi Na Pi Shenayim b'Ruchacha Elai" (2:9) was that two matters incumbent on Eliyahu, i.e. anointing Yehu and Chaza'el, Elisha will do them. Even though it is punishment, Elisha wanted to do so, to avenge the blood of Nevi'ei Hashem. Initially the decree was to do so in the lifetime of Achav's son; via Teshuvah, it was delayed.
Why should he go to Ramos Gil'ad? Melech Aram ruled there! Achav went to take it back, and he was killed. We do not find that a Melech Yisrael took it afterwards!
Radak: Perhaps Yisrael were in a camp outside the city, intending to take it back; Melech Aram was in the city. Melech Yisrael was stricken there; he went to Yizre'el to recuperate, and left the camp there. The Shali'ach should anoint Yehu in the camp 1 .
Radak: We must say that a Melech Yisrael took it afterwards - Yeho'achaz 2 or Yehoram. Chaza'el went to take it, and Melech Yisrael went there with his camp.
Radak: This cannot be. It seems that Yisrael were in the city. It says to bring Yehu "Cheder b'Chader" (to an inner room), "va'Yavo ha'Baysah", "El Gerem ha'Ma'alos", "Al Yetzei Falit Min ha'Ir Laleches Lehagid b'Yizre'el" (verses 2,6,13,15). These show that Yisrael were in the city, and Aram outside!