Tire tracks were still visible on Sunday at West 103rd Street and South California Avenue in West Beverly, where O'Shea said a car caravan gathered after spreading word on social media.
Neighbors said several yards and a country club were damaged.
Drivers allegedly raced at other several sites, too. ABC7 spoke with one man who described seeing "skid-outs."
Chicago police are reviewing surveillance video in the area to identify other vehicles involved, O'Shea said.
INTERACTIVE SAFETY TRACKER Track crime and safety in your neighborhood