Demonstrators gathered at Federal Plaza Monday evening in protest of President Trump's plan to send federal agents to Chicago to crackdown on violence.
The president tweeted over the weekend what some have taken as a veiled comment that federal help could be sent to multiple cities, including Chicago.
"Look at Portland, where the pols are just fine with 50 days of anarchy," he tweeted. "We sent in help. Look at New York, Chicago, Philadelphia. NO!"
The Trump administration deployed militarized federal agents to Portland despite protests from local officials.
In Chicago, Refuse Facism, along with half a dozen other groups, protested what they called "escalating problems."
"We are witnessing a major escalation toward a police state in this country," said Jay Becker with Fascism Chicago.
Facing threats federal agents will be sent to the city, Mayor Lightfoot said on MSNBC Monday evening that democracy is at stake.
"That's not going to happen, and I will use all my power to stop them," Lightfoot said on Joy Reid's "The ReidOut."
Earlier in the day, the mayor sent a letter to President Trump, blasting his "unhelpful" rhetoric and outlining ways she believes the federal government can help Chicago in an effort to reduce violence.
In the letter, Lightfoot asked for help in the following areas: common sense gun safety reform, public safety support, community outreach and community investment.
John Catanzara, the president of Chicago's Fraternal Order of Police Lodge 7, has also pleaded to the White House for help in combating violence.
In his own letter to President Trump, Catanzara said Lightfoot has "proved to be a complete failure who is either unwilling or unable to maintain law and order here."
More than 60 people were shot in weekend gun violence across Chicago. At the same time, Clashes near the Christopher Columbus statue in the city's popular Grant Park resulted in 49 officers being injured and a dozen individuals being arrested, according to Chicago police officials.
Police officers on bikes and protesters appeared to be at odds again Monday night - as protesters stopped traffic while marching throughout downtown.
"You can express your constitutional rights and your freedoms without threat or fear of being harassed," said Bishop Gregg Greer, Freedom First international organizer.