In 1862, Chickering became a colonel during the American Civil War, eventually being awarded the honorary grade of brevet brigadier general.

[3] For several years before the Civil War Chickering had been interested in the military and commanded a company, the New England Guards, in the state militia.

The regiment was deployed to New Orleans in November 1862 as part of Major General Nathaniel Banks's Louisiana expedition.

During April and May 1863, the 41st Massachusetts was part of an expedition to Opelousas, Louisiana, to forage for supplies and gather freed slaves by the thousands for recruitment into the Union Army.

Chickering was appointed military governor of Opelousas and commanded the Union troops (consisting of seven regiments of infantry) that were part of the expedition.

[6] For his service during the war, Chickering was awarded the honorary grade of brevet brigadier general, nominated February 21, 1866, confirmed April 10, 1866, to rank from March 13, 1865.

[10] The "famous" hall, according to The New York Times, stood on the northwest corner of Fifth Avenue and 18th Street.