By 6 p.m. Friday, several hundred people had gathered in Logan Square Park with plans to march to Mayor Lori Lightfoot's house nearby, though police barricades kept them from getting too close.
WATCH | Hundreds of demonstrators gather in Logan Square to demand justice for Adam Toledo
The group grew to thousands as they marched through the neighborhood, shutting down the six-corner intersection of Milwaukee, Diversey and Kimball around 7:30 p.m.
Many in attendance said they were there to protest a system of policing that simply isn't working, and they wanted the mayor to hear that message.
RAW VIDEO | Protesters clash with police in Logan Square
"On social media, there's a ton of people that still deny this is even an issue, and so if you stop showing this, conversation stops," Chicago resident Gerald Parker said.
The event was largely peaceful, but as it came to an end around 10 p.m., a small group of protesters still lingering in the streets began scuffling with police.
RELATED: Chicago Police Officer Eric Stillman, who fatally shot Adam Toledo, had 3 misconduct complaints in 5 years with CPD, watchdog group says
At least two people were arrested in connection with the protest.
Anthony McCullom III, 20, was charged with misdemeanor reckless conduct for allegedly being part of a large crowd seen pushing and shoving officers just before 10 p.m. in the 2600 block of North Kedzie Avenue, according to police.
McCullom's mother, Black Lives Matter Chicago Executive Director Amika Tendaji, said her son was trying to stop officers from attacking protesters when he was put in handcuffs.
"There was nothing that happened out there that warranted the arrest of any young people who were out there fighting for their lives," Tendaji said. "They (the police) were brutal to those protesters and there are no signs of it slowing down."
Also arrested during the protest was Graham Lefauve, 18, who allegedly rode by on a bicycle and spat on an officer who was in an unmarked squad car, police said. Lefauve was charged with misdemeanor battery.
The protest was peaceful except for a few dustups toward the end of the night.
It was the city's first major demonstration since authorities released videos of Adam's final moments, apparently showing the boy with a gun just before the shooting - but with his hands raised and empty at the moment the officer shot him in the chest.
Tendaji said McCullom was being held at the 25th District Station and was "probably terrified."
"I don't want any more family members experiencing this. He's in a cell with the same people who showed no remorse in killing a 13-year-old," she said. "If folks keep getting arrested, the idea is that we will be too afraid to keep fighting back, but at this point we have no choice. We're fighting for our lives."
Activists continue to call for police reform, and Mayor Lori Lightfoot said she wants Chicago police to have a revised policy in place before summer, as the Adam Toledo case has critics calling out the city for resisting reform on foot pursuits for several years.
Ahead of Thursday's emotional events, the city and some businesses prepared for the possibility of violence. Windows were boarded up and city vehicles stood ready to block traffic, scenes reminiscent of last spring, after George Floyd died in Minneapolis police custody.
RELATED: Video of teen killed in Chicago police shooting released by COPA
An online vigil is scheduled for Saturday night, and a small peace walk is expected Sunday, but Chicago police are prepared for the possibility of more protests throughout the weekend.
The Sun-Times Media Wire contributed to this report.