The protesters ranged from children to senior citizens of various races and backgrounds from across the country. Their concerns were echoed in their chants "We reject the president-elect," "No hate, no fear, immigrants are welcome here," and "Our body, our choice."
Major issues of concern for Chicagoans, who historically vote Democrat, include immigration, LGBTQ rights, and women's health.
Protests began at 10 a.m. local time (1600 GMT) at Millennium Park, a major tourist destination, and caused street closures when they marched toward the Magnificent Mile, the city's famous shopping area. Protesters held signs reading "Refugees welcome," and "Not my president."
"He doesn't represent how we think or feel in Chicago," said Dan Milam, a 20-year-old animal caretaker, who works five days a week and used his two days off to protest.
"We're letting everyone know that he doesn't represent how we look at foreigners. We're saying that we're here for each other in the most divided time in America since the Civil War. We're saying we won't accept xenophobia, racism, sexism, or homophobia in Chicago," he said.
Chicago police set up barricades in front of Trump Tower to prevent protesters from getting close. Protesters marched up and down State Street and Michigan Avenue, two streets with heavy foot traffic from tourists.
Community activists scheduled multiple protests on Saturday, some of which converged and created bigger protests.
The constant protesting gave people who were on their way to and from work or school an opportunity to jump in and protest when they could, like Catina Deubler, a 22-year-old student at the School of the Art Institute of Chicago.
"We are making ourselves heard because his beliefs and tactics are disgraceful. Trump may have been representing a category of American people who have felt silenced these past eight years, but it is unacceptable to feed off fear and hatred to win. He has divided our country and we are badly hurting," Deubler said.
Protests continued late into Saturday night and more protests are expected in the coming day.
Chicago is just one of the major US cities protesting against Trump. Protesters know these demonstrations will not change the outcome of the election, but hope to at least send a message to the president-elect.
XINHUA/MNA