Memorial Day weekend's violence started within hours of superintendent David Brown announcing on Friday plans to contain the violence.
By Monday, 10 people were killed and 39 people were wounded.
On Tuesday morning, Brown said people have been cooped up because of the coronavirus outbreak and are restless.
"This unacceptable level of violence happened while Chicago remains under the stay at home order meant to prevent the spread of COVID-19," Brown said.
Brown had announced an all hands on deck strategy with beefed up police patrols, but on Tuesday Mayor Lori Lightfoot made it clear more needs to be done.
"I know that there was a lot of energy and coordination among a variety of groups. What I said to the superintendent this morning is, this was a fail," Lightfoot said. "And whatever the strategy is, it didn't work."
Meanwhile, CPD is under fire after an Instagram video surfaced showing officers breaking up a large crowd Sunday night in Englewood.
Chicago police said they were trying to disperse the crowd when an officer noticed a man holding a gun and then there was a chase. The man was taken into custody a short time later.
Shots were fired in the area and a second person was taken into custody, police said.
No one was injured by gunfire but two officers were injured and transported to the hospital in good condition, police said.
Three men, all in their 20s, have been charged in the incident so far. One was charged with aggravated assault to a state employee, two were charged with disorderly conduct, two were charged with physical battery, and all three were charged with resisting or obstructing a police officer. All charges are misdemeanors.
The incident caught the attention of Lightfoot, who wrote on Twitter, "We will continue to investigate the incident to ensure proper tactics were used - ensuring constitutional rights are protected and that CPD officers are wearing face coverings."
I have seen a widely shared video of an incident in the 007th District. We will continue to investigate the incident to ensure proper tactics were used—ensuring constitutional rights are protected—and that CPD officers are wearing face coverings to maintain public health.— Mayor Lightfoot #StayHomeSaveLives (@chicagosmayor) May 25, 2020
It also caught the attention of Chance the Rapper, who tweeted, "Please stop sending large groups of militarized police into our neighborhoods exclusively."
Lightfoot disputed that narrative in her own tweets, saying police "responded to dozens of reports of social distancing violations in every part of Chicago."
Yo I seen HUNDREDS of ppl at millennium park and and pics of even more at the parks on the north side. Outside, no masks, no social distancing, enjoying themselves. Please stop sending large groups of militarized police into our neighborhoods exclusively https://t.co/mnAUSCsevy— Chance The Rapper (@chancetherapper) May 25, 2020
As officers enforced social distancing rules, Brown said 300 group dispersal notices were issued each day of the long weekend.
CPD Superintendent David Brown speaks after violent weekend, stay-at-home order dispersals
"I want the community to understand the challenges officers face when saving lives and tamping down violence crime," Brown said.
Lightfoot followed up to her tweets over the weekend that officers were only breaking up crowds in communities of color, adding that they were sent all over the city.
Lightfood said that officers face unprecedented challenges in maintaining public safety in the age of COVID-19
"This is probably one of the most difficult times of policing that we've experience in the city that goes back 20 plus years," Lightfoot said.
Monday, protesters in Millennium Park were dispersed by police after gathering too closely as well.
City officials said the protesters had not acquired, or made any attempt to acquire, a permit to protest on Chicago Park District property, and that the dispersal was peaceful.