The incidents occurred at an overpass in the 11700-block of South Michigan Avenue at about 1:01 a.m., police said. The windshields on at least five vehicles were damaged, police said.
"I was coming from under the viaduct, coming off of work, and a brick just hit the side of my car and came through the window," said Jasmine Moore.
No one was injured and no one is in custody, police said.
In a separate incident, three boys were charged after a Chicago police vehicle was hit by rocks in the Little Village neighborhood.