Chicago was ordered as part of the "ABCD" ships, the others being the cruisers Atlanta and Boston and the dispatch vessel Dolphin.

All were ordered from the same shipyard, Delaware River Iron Ship Building and Engine Works of Chester, Pennsylvania.

She had fourteen 100psi boilers that ran two compound overhead beam steam engines that producing 5,084 ihp (3,791 kW) to turn her two screws and achieve a speed of 14 kn (16 mph; 26 km/h).

The cruiser served in European and Mediterranean waters as the flagship of the Squadron of Evolution until 31 May 1890, when she sailed from Funchal, Madeira to call at Brazilian and West Indian ports before returning to New York on 29 July.

With the squadron, she cruised in northern European, Mediterranean, and Caribbean waters until 1 August 1903, when she proceeded to Oyster Bay, New York, and the Presidential Review.

After operating along the northeast coast, the cruiser departed Newport News on 17 November for Valparaíso, Chile, arriving on 28 December.

There, on 1 January 1905, she relieved the armored cruiser New York as flagship of the Pacific Squadron and for three years operated off the west coasts of North and South America, in the Caribbean, and to Hawaii.

Arriving from San Diego at 6pm on 19 April, Chicago's radio allowed the city's leadership to communicate with the outside world, as telephone and telegraph lines were down.

The removal of 20,000 refugees to Tiburon in Marin County by this ship and numerous other vessels is said to be unparalleled and unsurpassed until the 1940 evacuation of Dunkirk.

On 6 April 1917, Chicago was placed in full commission at Philadelphia and reported to Submarine Force, Atlantic (COMSUBLANT) as flagship at New London, Connecticut, commanded by future Admiral Thomas C.