Residents and business owners are working to assess the damage and begin the cleanup process.
WATCH: Chicago mayor, police respond to overnight looting downtown
The Binny's liquor store south of downtown was one of the many stores destroyed.
Shattered windows, cash registers ripped from countertops and a trail of liquor bottles is just some of the damage the can be seen scattered on the streets as the looters grabbed anything and everything they could.
The store safe at the Binny's was spared, but it appears there was an attempt to take it. Suspects managed to rip it out of the wall but were apparently unable to open it so they left it behind on the floor.
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Looters also broke into the wine cellar and stole bottles of Dom Perignon, but left behind a lot of very expensive bottles of wine without well-known brand names.
The Target on Roosevelt Rd. also appeared to be broken into.
A neighborhood volunteer was seen busy cleaning up the mess that included boxes and Styrofoam from big-screen TVs that have been stolen out of the side door of the store.
Wigs from a beauty supply shop in the area were also stolen from the front window display, but it seems most everything else in the store was left alone.
The recent looting attack has the Chicago-area reeling after just beginning to recover from June's crime spree.
Community members said they are concerned what happened Monday morning could grow into something much worse if city leaders do not take firmer action.
Reaction to the violence and destruction has been a mix of sadness and anger.
"We've got to start shedding light on the real problems of why people can feel they can act this way out of frustration," said South Side community activist Ja'Mal Green.
The looting played out hours after a Chicago police-involved shooting in Englewood.
RELATED: Englewood police shooting may have sparked Chicago looting, some residents say CPD raised tensions at scene
Misinformation about the shooting shared on social media prompted groups to organize car caravans dispatched to target certain businesses.
"If we hear that people are organizing to go downtown, I don't understand how we did not stop it before it happened," said Father Michael Pfleger from St. Sabina Catholic Church. "I'm not blaming police, but if we had the information why didn't we stop it and if we didn't know it, why?"
While several community leaders said they did not condone the looting, they understood the frustration driving the crime.
Mark Carter, a West Side community activist, said the cycle will not end until people in the neighborhoods can get good paying jobs, affordable housing and resources.
"I'm saying to the people again down here downtown, link with us so we can put pressure on this administration to keep these young people in their community and open up opportunities right there in their communities where they don't have to come down here to survive," Carter said.