The mayhem caused the city to raise bridges to cut off access to downtown, according to photographs and video footage.
“We are waking up in shock this morning,” Mayor Lori Lightfoot, a Democrat, told reporters in a press conference on Aug. 10.
Dozens of people “engaged in what can only be described as brazen and extensive criminal looting and destruction,” she said.
The rioting started late Aug. 9, Chicago Police Superintendent David Brown said. It appeared to stem from outrage over a police shooting earlier in the day.
Officers responded to a call in the Englewood neighborhood about a man with a gun and tried to interview him but he fled. As he was moving away, he pulled out a firearm and fired shots at the officers, who returned fire.
The 20-year-old man was rushed to the hospital.
A crowd gathered in the area and began shouting at the police.
“Tempers flared, fueled by misinformation as the afternoon turned into evening. CPD became aware of several social media posts encouraging looting downtown,” Brown said.
Four hundred officers were dispatched to try to stop the looting but dealt with so-called car caravans streaming into the heart of the city, targeting dozens of stores, including a Best Buy, an Apple store, and clothing businesses.
More than 100 people were arrested on charges including burglary and disorderly conduct.
Some looters resisted arrest. Thirteen officers were injured, including one who had his nose broken while fighting with criminals.
While officers were arresting one looting suspect—who was walking out of a store with a cash register—a vehicle passed by them, and someone inside opened fire. Officers returned fire. It wasn’t clear whether anyone inside the car was struck, and none of the officers were hit.
Elsewhere, a security guard and civilian were struck by bullets. Both were hospitalized in critical condition.
Officials vowed to hold criminals responsible for the crimes and urged the public to help them identify the looters.
Harsh measures are being imposed to try to prevent another night of unrest. Access to the downtown is being restricted from 8 p.m. to 6 a.m., with an enhanced law enforcement presence staying in place until further notice.
“CPD will not stand by as our beautiful downtown becomes someplace that people fear,” Brown said.
The police department is creating a special team to pour over the hours of surveillance footage that shows the looting.
Officials described the looters as confident they could break into stores and face no consequences. Some of those arrested during rioting in the summer were released with little or no repercussions, Brown said.
“These looters, these thieves, these criminals are emboldened by no consequences in the criminal system. They get released. Many charges get dropped. And so they feel emboldened to do it more,” he said. “We would argue that, let’s have the criminal justice system here deliver a strong message to these criminals, that there will be consequences for their behavior.”