[1] He gained military experience in the fight against the rebellious Cossacks during the Severyn Nalyvaiko's uprising under Field Crown Hetman Stanisław Żółkiewski.

[2] His crowning achievement was the great victory near the Daugava in the Battle of Kircholm (modern Salaspils) on 27 September 1605, when, with barely 4,000 troops, mostly the Winged hussar heavy cavalry, he annihilated a Swedish army three times the size of his force.

[2] For that feat he received letters of congratulation from Pope Paul V, most of Catholic royalty, and even the Sultan of the Ottoman Empire and the Shah of Persia.

[2] Soon afterward, he was rewarded with the rank of Lithuanian Grand Hetman, in addition to a number of royal land grants and leases.

[2] Yet this great victory was virtually fruitless, owing to the domestic dissensions; the Sejm (Commonwealth parliament) failed to agree on raising the funds needed for the war effort.

[2] Chodkiewicz was one of the magnates who remained loyal to king Sigismund III Vasa, and helped him to defeat the Zebrzydowski rebellion in 1606–1607.

Instigated by King Sigismund III, the war was unpopular among Lithuanian magnates, and Chodkiewicz was no exception; in fact his displeasure was so public and significant that he lost the royal favor for a time.

[3] Over the next few years, in the period of 1613–15, Chodkiewicz defended the Commonwealth gains in the Smolensk area, and dealt with unrest in Lithuania.

[3][4] An army of 160,000 Turks and 60,000 Tatars led by Sultan Osman II in person advanced on the Polish frontier.

[3] Chodkiewicz crossed the Dnieper in September 1621, and entrenched himself in the Khotyn Fortress, directly in the path of the Ottoman advance.

[3] Dobrowolska notes that he was an energetic and explosive antithesis of the composed Żółkiewski, another great hetman of this era, whom Chodkiewicz disliked and competed with throughout his life.

[7] His life was dominated by warfare, if not on the front lines, then on the political scene against other Lithuanian magnates, particularly the Radziwiłł family and the Sejm politicians whom he held responsible for not passing enough taxes to support the armies he wanted.

[7] He strongly believed his service should be rewarded with land grants, but he would simultaneously often use his own money to pay for military expenses.

[7] He was one of Wacław Potocki's characters in his epic novel on the Khotyn war (Polish: Transakcja wojny chocimskiej), and he also appeared in the works of Julian Ursyn Niemcewicz and Zofia Kossak-Szczucka, usually portrayed as a patriot and military genius.