By 6 p.m., 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
Justice for Adam Toledo rally held in Logan Square
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.
"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.
RAW VIDEO | Protesters clash with police in Logan Square
RAW VIDEO: Adam Toledo protesters scuffle with police in Logan Square
The night before, dozens took to the streets, protesting police and calling for justice for Adam Toledo downtown and in the West Loop. One group marched from Millennium Park up Michigan Avenue to the Magnificent Mile.
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Later, others made their way through the West Loop. Both protests briefly blocked traffic and then there was a protest right outside Chicago Police Headquarters.
"He put his hands up and was still murdered. So I have a question: what more could he have done?" said Rabbi Michael Ben Yosef, Chicago Activist Coalition for Justice.
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"I want to say to the momma, I'm here with you in solidarity. We will fight with you all the way," said Gloria Pinex, whose son was killed by a Chicago police officer.
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Nowhere has reaction to that tape been more visceral than Little Village, the working class Latino neighborhood where Toledo was born and raised.
RELATED: CPD shows Toledo video compilation to media ahead of public release
CPD shows Toledo video compilation to media ahead of public release
After demanding to see the video for weeks, residents openly sobbed on the street. Some said they couldn't bring themselves to watch.
Little Village pastor reacts to Adam Toledo shooting video
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"When I seen the video today, something inside of me died," said Kristian Armendiaz, Little Village Community Council. "I couldn't even bear to watch the whole video by myself. I felt like my childhood just died."
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"When they saw that video today, I thought about my three kids. I thought about the teenagers, the youth of Little Village. We need to start funding the community," said Maria Castillo, Little Village resident.
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.