Hundreds of people gathered to represent not just the city's labor movement, but a variety of advocacy and community groups, as well.
Organizers said they are taking a stand against what they call "the Trump led billionaire takeover of government."
"We're going to defend our democracy in the city of Chicago. We're going to protect the humanity of every single person in the city of Chicago," Johnson said.
The march began with a rally at the Haymarket Memorial sculpture in the West Loop.
The sculpture commemorates the bombing of a crowd on the evening of May 4, 1886. The crowd was protesting the violent deaths of workers during a labor lockout.
It followed a route that took it past three spots that protesters say are linked to President Donald Trump in some way, including a private investment firm and a Target. They're demanding a government at all levels that puts, in their words, "workers over billionaires."
A Tesla dealership was among the stops included on Monday's march, as well.
SEE ALSO | Here's what's open and closed on Labor Day 2025
They carved their way through Fulton Market and the West and South loops.
"They are redrawing lines in Texas. But in Chicago we put a line in the sand to say, 'if you mess with our workers, you mess with America,'" Pastor Jamal Bryant said.
With the threat of an imminent National Guard deployment looming over the city this week, the Labor Day protest was about so much more than just workers' rights.
Organizers said there were around 1,000 people there.
"You want to attack workers and spread lies about Chicago, we're not going to take the bait. We're not extras in your little show," said Bob Reiter, president of the Chicago Federation of Labor.
The march sought to protest the Trump administration's policies across the board.
"I'm here basically to be vocal against the Trump administration and everything he is doing to our country, our workers and our environment," protester Mimi Ruther said.
Mayor Brandon Johnson speaks at 2025 Chicago Labor Day rally
There were also protests in Lake and McHenry counties and near Trump Tower in Chicago.
At one point, they started blocking the street. Police could be seen escorting people away from the area, but it's not clear if anyone was charged.
The White House did not respond to the protests Monday, but put out a statement that said in part: "...President Trump stands as the champion of the American Worker. From surging native-born employment and rising blue-collar wages to innovative workforce initiatives like expanded apprenticeships and trade school funding, the Trump Administration is reversing decades of neglect and finally putting American Workers first."