The first USS Chicago (later CA-14) was a protected cruiser of the United States Navy, the largest of the original three authorized by Congress for the "New Navy" and one of the U.S. Navy's first four steel ships.

Chicago was ordered as one of the "ABCD" ships, the others being the protected cruisers USS Atlanta and USS Boston and the dispatch vessel USS Dolphin. These were the Navy's first steel-hulled ships, and their ordering is generally taken to mark the beginning of the "New Navy."

Chicago was built with a displacement of 4,500 long tons (4,572 t) at an overall length of 342 ft 2 in (104.29 m) and 325 ft (99 m) at the perpendiculars. Her beam was 48 ft 3 in (14.71 m) with a draft of 19 ft (5.8 m). She had fourteen 100-psi boilers that powered two compound overhead beam steam engines, producing a total of 5,084 ihp (3,791 kW) to turn her two screws and achieve a speed of 14 kn (16 mph; 26 km/h). Chicago was capable of carrying 830 short tons (750 t) of coal. Like the other "ABCD" ships, Chicago — rigged as a bark — was built with a sail rig to increase her cruising range.

Chicago's original armament consisted of four 8-inch (203 mm)/30 caliber Mark 2 guns, eight 6-inch (152 mm)/30 caliber Mark 2 guns, two 5-inch (127 mm)/31 caliber Mark 1 guns, two 6-pounder 57 mm (2.24 in) guns, four 3-pounder 47 mm (1.85 in) guns, two 1-pounder 37 mm (1.46 in) Hotchkiss revolver cannon, and two .45 caliber (11.4 mm) Gatling guns.

She had 4 in (100 mm) of armor on her gun shields, 1.5 in (38 mm) on her deck, and 3 in (76 mm) on her conning tower.

All four "ABCD" ships were ordered from the same shipyard, John Roach & Sons of Chester, Pennsylvania. However, when United States Secretary of the Navy William C. Whitney initially refused to accept Dolphin, claiming her design was defective, the Roach yard went bankrupt and Chicago's completion was delayed for about three years while the Roach yard reorganized as the Delaware River Iron Ship Building and Engine Works.

Chicago was launched at Chester on 5 December 1885 at the Delaware River Iron Ship Building and Engine Works, sponsored by Edith Cleborne, the daughter of U.S. Navy Medical Director Cuthbert J. Cleborne. Chicago was commissioned on 17 April 1889.

Between 1895 and 1899 Chicago was refitted at the New York Navy Yard, with her main batteries replaced by four new 8-inch (203 mm)/35 caliber Mark 4 guns, and with all secondary 6-inch and 5-inch guns replaced by fourteen new 5-inch (127 mm)/40 caliber Mark 3 guns. She had her sails removed, boilers replaced by six Babcock & Wilcox and four cylindrical boilers, and engines replaced with two horizontal triple-expansion engines totaling 9,000 ihp (6,700 kW) for 18 kn (21 mph; 33 km/h) speed. In 1902 she was partially reconstructed, with an extended armored deck and increased displacement of 5,000 long tons (5,080 t). In 1915 as a training ship she was rearmed with twelve 4-inch (102 mm)/40 caliber guns, and in 1918 as a flagship with four 5-inch (127 mm)/51 caliber guns. In 1920, as a submarine tender at Pearl Harbor, she was disarmed.