The crowd of demonstrators grew steadily throughout the afternoon. Two groups of protesters gathered initially at either Daley Plaza or near Trump Tower around 4 p.m. Marching began around 4:30 p.m. as the two groups met up, and the crowd continued to grow as the evening wore on.
When the pack of protesters made it north of the river, blocking busy streets in River North, things got heated.
"She had been pulling this cart all evening, and he just, as soon as the lady in the wheelchair got to the side he just gunned it, just went down the street and just ran her entire thing over," said a protester.
A passerby and a protester nearly came to blows on the sidewalk. Someone in the crowd shattered the windows of a bank on Michigan Avenue. Chicago police said a total of 16 people were arrested in Friday's protests.
Those protesting said they will not be silent over the next four years. The demonstrators marched around the Loop, up State Street, past Trump Tower, and eventually out onto Lake Shore Drive, blocking traffic along their way.
The group of dissenting voices against Trump have grown louder and more emphatic in the hours since he was sworn in as president. Chicago native Theresa Deeb flew from London to join the protests.
"Every day I walk outside, somebody hears my accident and the very first question, no joke, is 'What's going on? What about Trump?'" she said.
Franky Rosenthal and her friends aren't old enough to vote, but they attended the protest to make their views clear.
"I think this protest will make him realize how upset this truly makes us. That we're not going to stop talking and we're not going to stop speaking until he does something about how he's going to run this country," she said.
Amongst the anti-Trump demonstrators, one Trump voter, who declined to give his name, stopped to listen.
"We need to support the man who is going to be leading our country for the next few years," he said.
Still, he said he was listening to what the protesters were saying and trying to understand them.
Chicago will host a local Women's March Saturday, a reflection of the massive Women's March on Washington. Organizers have said approximately 50,000 protesters are expected to attend here; organizers in the nation's capital are expecting at least 200,000.
STUDENTS WALK OUT IN PROTEST OF TRUMP
Earlier in the day, students at the University of Illinois - Chicago made a political statement on campus.
"Just like everyone else on campus, I feel very against the new president-elect and just angry, and it's just one of the ways I can speak out and feel like I have a voice," said Paloma Esparza, UIC student.
This is not the first time UIC students have come out against Trump. In March 2016, the then-candidate was forced to cancel a campaign rally at the UIC Pavilion after thousands of protesters showed up. The campaign cited security concerns.
"We were glad to have been able to do that and we want to keep doing that. We want to keep empowering students. We want to keep empowering young people," said Julian Rojas, UIC student.
Some Chicago high school students walked out of class in protest. Crane High School freshman Daysha Del Valle led the efforts at her school while her mom stood and watched in the background.
"Of course this school is primarily minorities - black, Latino and Asian. We are inspiring them to walk out," she said.
"This sends a really big message to these young students, they are really waking up and they are not going to tolerate disrespect, especially from our president," said Anita Rico, parent.
The United Working Families political party organized what they're calling a "people's assembly" to figure out the plan for the next four years.
"We know folks are hungry for a space to connect with each other. People have a lot of anger at this incoming administration, a lot of fear, and this event today is to channel those feelings and move people in action together," said Amisha Patel, United Working Families.
The crowd in Daley Plaza was comprised of diverse people and groups.
"I need to stand up against hatred, bigotry and racism. That's our new president and what he stands for," Dianne Arp, protester.
"I've been a voter and participated in elections as long as I can remember and I've never ever been this frightened about a new president," said Denise Nora, protester.