For most of fall, Trump’s immigration agents have set out every day to scour Chicago neighborhoods where immigrants live. On Friday, Operation Midway Blitz fanned out across the wealthier white communities on the North Side where they work.

Throughout the day, caravans of federal agents hit neighborhoods that had so far avoided serious confrontations.

In Lakeview, agents threw tear gas into the street even as their use of chemical agents has drawn intense scrutiny from a federal judge. Masked officials arrested a man at the Laugh Factory comedy club. They detained a man at a gas station near the tony Latin school where the city’s elite send their children.

What to know about Donald Trump’s immigration enforcement raids in Chicago

Lincoln Park Ald. Timmy Knudsen, 43rd, said masked immigration agents hit “every corner of the ward” he represents, one of the city’s wealthiest communities. A video taken at Racine and Schubert Avenues shows four agents surrounding a Latino man and leading him away from million-dollar properties, placing him into an SUV and driving off.

Ald. Scott Waguespack, 32nd, said agents grabbed a landscaper and two construction workers and appeared to be going through side streets picking up workers. He got into a shouting match with an immigration agent near St. Mary of the Angels school because they were doing U-turns and “driving like lunatics” near children doing a fun run.

Knudsen approached masked agents in another area and asked them questions he learned through “know-your-rights” trainings as well as his previous work handling asylum cases.

“What are you doing here? What are you looking for? Do you have a warrant?” he said he asked.

They didn’t respond.

Instead, activists confronted agents, shouting at them and blowing their whistles to alert the community.

“My hope is them whistling and yelling at least keeps ICE moving along,” Knudsen said.

Midafternoon, agents tear gassed the Lakeview neighborhood near Lakewood Avenue and Henderson Street after a crowd of residents demanded they leave.

Neighbors and congressional staff said the chaotic scene unfolded when federal immigration agents arrested at least one construction worker at a home on North Lakewood Avenue.

Employees appeared to be on a lunch break out front when agents jumped over the gate to get to them, residents told U.S. Rep. Mike Quigley’s office.

A resident of the building, visibly overwhelmed, declined to comment Friday afternoon.

The home was left half-finished with at least four ladders hanging on the side of the building and tape in the windows.

Neighbors with whistles confronted the ICE agents and demanded they get out.

Videos from the scene show two vans used by the agents, one of which is slowly driving backwards. Most of the gathered residents were on the sidewalk with a few walking in the street near the vehicles, chanting “traitors” and “go home.” They didn’t appear to touch it or the agents before tear gas is deployed.

Bruce Turner, 64, came outside when he heard the commotion and called the tear gas use “unprovoked.”

“They have one car going backwards, one car going forward, and people are … yelling at them,” he said. “Nobody touched them.”

Another resident, who declined to give her name for fear of retribution, said she was at home working when she heard screaming and whistles, telltale signs that preface ICE sightings. She, too, criticized the feds’ use of tear gas.

“There was no warning, no warning at all,” she said.

Ald. Bennett Lawson, 44th, who represents Lakeview and Wrigleyville, released a statement condemning the actions.

“ICE’s un-American and undemocratic tactics of fear and intimidation in our neighborhoods are a direct attack on everything Chicago stands for — inclusion, compassion and love,” Lawson said. “We have a proud history of welcoming people of all backgrounds in our community and our commitment to those principles are stronger now than ever.”

Outside the Nettelhorst Fine and Performing Arts School on Broadway Avenue in Lakeview, a neighborhood resident volunteering as an ICE-watcher kept an eye out for agents. While the neon vest-clad volunteer stood guard, a man dropped off a set of orange whistles into a Little Free Library box outside the school. He said he was 3-D printing the whistles by the hundreds.

Videos circulating on social media showed agents within blocks of DePaul University. In a message to students and faculty Friday, its president Robert Manuel said the school had received confirmed reports of nearby federal immigration activity. He noted classes, research and other campus activities are proceeding as scheduled.

“The safety and well-being of our students, faculty, and staff are our highest priority,” Manuel wrote. “Now more than ever, we must look out for one another.”

The Laugh Factory in a social media post Friday said that one of its employees was among those detained. Per the comedy club, its night manager was detained by “masked federal agents” outside of its Lakeview location at 3175 N. Broadview St. The club did not return immediate requests for comment.

Earlier this week, federal immigration officials were in Little Village — a Southwest Side neighborhood that is home to Chicago’s largest Mexican American population — on Thursday for the second time in two days. Half a dozen people were detained in the raids Thursday, including a 16-year-old U.S. citizen, a student at Benito Juárez Community Academy in the Pilsen neighborhood. At least seven people were also taken into custody Wednesday.

This is a developing story.

Chicago Tribune reporters Talia Soglin, Kate Armanini and Kate Perez contributed.