CHICAGO — Looming over the tapestry of flags and homemade signs undulating across the lawn of Grant Park on Saturday were two that stood higher than the rest.

Robert Ryan, 61, had meticulously fashioned both a “NO KINGS” flag — complete with an angry red X crossing out a crown — and the signature Chicago flag atop a 15-foot pole.

He was one of more than 100,000 rallygoers who flocked to Grant Park late Saturday morning to take part in the nationwide “No Kings” demonstrations that later proved to be Chicago’s largest protest in recent memory. The event was organized in response to President Donald Trump’s administration, which has lately made Chicago ground zero for his mass deportation campaign.

Ryan lugged the flags from south suburban Joliet, taking the early 8:30 a.m. train to get to Grant Park on time. It was his fifth time protesting the Trump administration this year, he said.

“I feel it’s one of the only things I really can do, is add one person to the numbers,” Ryan said. “But at the end of it, I feel much better. I don’t feel sad. I feel glad I did something. I try to tell other people, you won’t regret it, and I never have.”

The No Kings “Hands off Chicago” protest was one of roughly 2,500 similar demonstrations against the Trump administration planned across the country and globe, according to event organizers.

The main Chicago rally and march kicked off at noon at Butler Field in Grant Park, located at East Jackson Drive and South Columbus Drive. A smattering of elected officials, including Mayor Brandon Johnson and Gov. JB Pritzker, addressed the crowd in the latest full-court press from local Democrats seeking to condemn the president.

Miles away, federal immigration agents were spotted detaining individuals at a parking lot for rideshare drivers at O’Hare International Airport, in what would be their second raid on airport grounds this month.

Just before 2 p.m., the crowd began a slow but spirited march around the Loop that, for many, doubled as an impromptu dance party, complete with a ragtag symphony of musical instruments and singing.

Some of the songs sampled include the American folk anthem “This Land Is Your Land” and “Do You Hear the People Sing” from the Les Misérables musical, both blasting from a tuba player. Meanwhile, marchers chanted, “ICE, ICE go away, immigrants are here to stay,” and “Hands off Chicago!”

Onlookers watched the parade from rooftop buildings and windows facing Michigan Avenue, peering over the ledges and pressing their faces against the glass. Some pedestrians stopped in their tracks and decided to join the march.

A masked man in all black stood atop the entrance to the Grant Park parking garage, vigorously waving an American flag flown upside down. In front of him, someone else was carrying a blown-up copy of the U.S. Constitution, the “We the People” opener neatly scribed at the top.

The sound of whistles — an ominous warning from neighbors in recent weeks that U.S. Immigration and Customs Enforcement was nearby — instead rang out from the crowd as a cheer.

During the earlier speeches, the mayor urged the throngs of attendees at Grant Park to keep protecting immigrants who live in fear of federal immigration authorities.

“There are those in this country that have decided, at the behest of this president, to declare war on Chicago and American cities across this country,” Johnson told the crowd, eliciting a chorus of boos. “They have clearly decided that they want a rematch of the Civil War. But we are here to stand firm, to stay committed, that we will not bend, we will not bow, we will not cower, we will not submit.”

When Pritzker took the stage, he looked onto the rally and declared, “That is what resistance looks like.”

“Donald Trump, stay the hell out of Chicago,” Pritzker said. “The fighting against tyranny isn’t won or lost in one protest. It’s won in countless daily decisions to stand for justice, to refuse cruelty, to defend human dignity. It’s won when we recognize that none of us are free until all of us are free.”

The nationwide demonstrations were the latest flashpoint in Trump’s ongoing immigration crackdown on Democratic-led cities, with Chicago serving as his biggest focal point for the deportations. Titled “Operation Midway Blitz,” the heavy ICE activity that began in September has disrupted livelihoods for many Latino communities around the Chicago area. Trump has saber-rattled a military occupation as well, but for now, the courts have blocked the White House’s attempts to deploy the National Guard to Chicago.

Among the aggressive tactics federal agents have been spotted enacting on the streets include tear gassing protesters and even Chicago police officers, as well as conducting raids and arrests that legal experts say are unconstitutional. But the U.S. Department of Homeland Security has argued that immigration enforcement is making cities like Chicago safer, even as crime has already been trending down for the past few years.

The No Kings demonstrations — the second of the year — were roundly condemned by Republican politicians as “Hate America” rallies. But the scene on Saturday was peaceful, though noisy, in downtown Chicago.

Ahead of the speeches, a DJ warmed the crowd up with protest anthems by Black Sabbath, John Lennon, Rage Against the Machine and Public Enemy. Boxes of miniature American flags for attendees to take lined the perimeter of the sidewalk.

Nick Ruzas, 34, held one of those flags ahead of the event, sitting and watching as organizers did sound checks on the stage.

For him, attending the protest is taking a stance against the “corrupt president” and what he said was a false narrative of Chicago being a “warzone.”

“Disappearing people off the streets, no due process, it’s insane. And bringing National Guard here when it’s not wanted … it’s ridiculous,” Ruzas said. “It’s like having a toddler as president.”

While the mood at the rally was largely positive — forecasted rain cleared out before the events began — many of the thousands of signs carried by attendees struck a darker tone, referring to ICE as “the new Gestapo” and referencing Trump’s ties to convicted sex offender Jeffrey Epstein.

Attendee Andrew Hayes, 35, said the stories he hears of ICE barging into restaurants and other places in the city he frequents do resemble tactics from the Nazi Germany regime.

“I got a lot of coworkers … their families are immigrants. I’ve got an apprentice who works for me. His family’s all from Mexico, so I know he does not — and I don’t agree with — what ICE is doing,” Hayes said. “Don’t care for this Gestapo-style snatching people.”

Cynthia Cortez, 27, had arrived around 9 a.m. with her mother, both traveling from west suburban Plainfield. Holding a hot pink sign declaring “March for those who run in fear,” Cortez said the duo believed in standing up for people who cannot fight for themselves.

“I can’t really stand by that. I can’t be on the wrong side of history,” Cortez said. “At this point, it’s pretty much you fight for the people. You fight for your rights. You fight for the families. It could be any one of us. We’re literally just one step away from that.”

Organizers of the Grant Park rally included Equality Illinois, Indivisible Chicago, Chicago Federation of Labor, Personal PAC, Sierra Club Illinois and the American Civil Liberties Union of Illinois. Dozens of other local No Kings protests are also scheduled throughout the Chicago area, including Naperville, Elgin, Highland Park, Valparaiso, Aurora and Gary.

Millions of protesters nationwide attended the first No Kings protests across the U.S. in June, with massive crowds of demonstrators filling the downtown Chicago event.

(The Tribune’s Angie Leventis Lourgos contributed reporting.)

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