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. 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.
"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.
SEE ALSO: What we know about the fatal police shooting of 13-year-old Adam Toledo
At least two people were arrested in connection with the protest.
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.
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.