The day began with a smaller group gathered outside Trump Tower. They stayed there for much of the afternoon until they were joined by a larger group of demonstrators. Chicago police asked the group to move to the corner of Wacker and Wabash, where they began marching.
The protesters split into two groups, one marching through the streets of the Loop, blocking traffic and surrounding cars when they could. The other group headed up Michigan Avenue to Lake Shore Drive, shutting down traffic in both directions for a time. Lanes reopened in both directions around 9:15 p.m.
The march then moved down into the South Loop and before looping back north to return to the heart of the Loop near Wacker and Wabash where it began.
Many of the protesters were young, many are minorities, and they said they're angered by the election results. They don't believe Donald Trump will be a president for all Americans.
"I will not tolerate that man as president of this country. I will not. I will never accept this. I don't know if it's two years until he gets impeached, if it's four years, if it's eight years, I will never accept this," said Kathy Rawson, protester.
"Donald Trump's America is not an America we want to live in. It's xenophobia, it's racism, it's homophobia, it's sexism. It's everything against what our democracy stands for," said protester Cooper Foszcz.
"You saw all of the hate was coming with him, and you were just hoping that that would never come to fruition, and it has," said Will Rossi, anti-Trump protester.
"We're just not happy about Trump. He's a bigot. We can't have that as the face of America. We're a joke of the world," said Sam Barber Kennedy, anti-Trump protester.
"I'm extremely upset that a bigot and a xenophobe and a homophobe and an Islamophobe got elected our president. It's appalling," said Jaye Rodriguez, anti-Trump protester.
The demonstration had attracted the attention of some Donald Trump supporters, and at time there's been some tension, some arguing. Police stepped in at one point. Many of the protesters are young, and the youth vote did not come out for Hillary Clinton in the same numbers as for Barack Obama. A significant portion did not vote, or voted for a third-party or write-in candidate. Some of these protesters say that should be a wakeup call.
GROUPS TARGETED BY TRUMP FEAR HIS PRESIDENCY
This is not what they expected.
Donald Trump spoke often during his campaign about tightening up the borders, keeping Muslims out, and building a wall on the Mexican border. Now those in the groups he frequently targeted with harsh rhetoric say they are scared.
In Chicago's Chinatown, business continues as usual. Residents - including many recent immigrants - are going about their lives. It's much the same in Pilsen, even though many Latinos who were targeted by Trump's campaign rhetoric are fearful about what his election could mean to them.
"I'm here to say it's okay to be sad, it's okay to cry, it's okay to be angry," said Imelda Salazar, Southwest Organizing Project.
"We're shocked, upset and we're in crisis mode, and we know that this is an open season on all of us," said Inhe Choi, Korean American Center.
When they planned the news conference weeks ago, leaders of immigrant groups expected to be celebrating. Instead, many said they are now fearful; worried about being discriminated against or, worse, deported.
"I think we have to prepare for the worst. We have to prepare to for Donald Trump to carry out his word," said U.S. Rep. Luis Gutierrez (D-IL).
The Illinois Coalition on Immigrant and Refugee Rights worked tirelessly to get new immigrants to the polls. And they got results; the number of new immigrant voters in Illinois was up substantially. But they still fell short of the result many of them were hoping for. In fact, nationally a significant percentage of Latinos voted for Trump.
"This idea of lumping Latinos into a Democratic group just on the basis of immigration is probably a mistake," said Wayne Steger, professor of Political Science at the University of DePaul.
Muslims were another target of Trump's campaign rhetoric, as he vowed to prevent them from entering the U.S. and increase scrutiny of those already living in the U.S.
"We have already instructed our mosques to beef their security, to make sure that their security camears are working, to have volunteers who can look around and monitor for suspicious people," said Ahmed Rehab, Council on American-Islamic Relations.
Steger said while more Latinos voted in this election than four years ago, a smaller percentage of them actually voted for Hillary Clinton than they did for Barack Obama in 2012.