Eight of the victims, mostly teenagers, were struck at 79th Street and Essex Avenue at around 9:30 p.m. local time (0230 GMT Friday), The Chicago Tribune reported.
Then two men, 27 and 33, were shot in the East 37th Street and taken to the University of Chicago Hospital. The younger man was shot in the head and the other in the right arm, police said.
Around the same time, two other men were wounded in the arms in a drive-by shooting in the West 39th Place in the Brighton Park neighborhood.
About 15 minutes later, a 24-year-old man was shot in the leg and taken to Jackson Park Hospital. The man told police he was talking on his phone when he heard a single shot and realized he was wounded.
Earlier Thursday evening, four men were wounded in a shooting in the Little Village neighborhood about 5:20 p.m. local time (2220 GMT). They were strolling along the South Kedzie Avenue, when at least one person inside a vehicle with three others opened fire. Three 19-year-olds and a 22-year-old were wounded.
Just after midnight, a 17-year-old was shot in the back and taken to Stroger Hospital in serious conditions, police said.
Another 17-year-old was shot after 1:30 a.m. local time (0630 GMT) on Friday in the 3500 block of West Grenshaw Street in the Homan Square neighborhood. He's in good condition at Mount Sinai Hospital. Someone walked to him and started shooting, police said.
Authorities have been battling an increase in homicides in Chicago, where some aldermen complain gangs have no fear of the police.
Nineteen people have been shot in at least seven shooting incidents across the US third most populous city of Chicago, with 13 people shot and wounded in a 30-minute spate of violence.