Video from the city's POD security camera, first obtained by CWB, shows the scene in the 400-block of State Street around 1:30 a.m. Saturday.
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It starts with shoving and what appears to be some kind of street argument, and quickly develops into a pile-on beating. There is no rush by bystanders or anyone else to stop the attack.
"The first one started beating him up, when he's done two started beating him up, and then four people beating him up," said William Salgado, witness who works nearby. "The poor guy, he couldn't even stand up."
Once the men are down, the unflinching crowd rob their pockets, even dragging them men and stripping them of their shoes.
"Things get so bad here at night we close at 10 on a Friday and Saturday," said Ross Garvey, manager of Hubbard and State Cigar Shop.
Residents and businesses said incidents like it are becoming more common in River North and the Near North Side.
"The bouncers from the different bars have been telling me they've been standing outside seeing people get shot, people using guns out here at 2 a.m.," Garvey said.
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"Car accidents, shooting, robbery, prostitution, rival gangs, everything," Salgado said. "Name it, it's out here."
"I think the video is brutal," said Steven Levy, president of Sudler Property Management. "What we're seeing today is the complete breakdown of a civilized society and these issues should be addressed by public officials."
The owner of the 7-11 on the corner showed video of the late night crowds in the story. She said employees have quit out of fear for their safety.
Sudler Property Management oversees nearly 40,000 residential units in the area.
"I've heard from many residents. They are concerned. Several have said they are afraid to go out at night," Levy said.
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The spike in crime led 42nd Ward Alderman Brendan Reilly to write a strongly worded letter to Mayor Lori Lightfoot.
"I am writing this to express my extreme frustration and concerns with the lack of overnight police resources downtown, and the dramatic spike in violent crime in our tourism and hospitality district at night," the letter read in part.
"We're losing business, tourists, they're afraid to come to eat right here, go to the bar, go here, walk," Salgado said. "If they don't, we're going to lose everything right here."
The Cook County Sheriff's Office will now have a more visible presence in the area, helping Chicago police.
"If we see something we can help out in, we will," said Chief Leo Schmitz. "We are there to deter. Hopefully we're deterring crime while we're there."