Meanwhile, communities are continuing on with Mexican Independence Day celebrations this week, and Illinois officials continue to criticize the president's actions.
Some 300 federal agents are using North Chicago's Naval Station Great Lakes as the logistical hub for ramped-up operations, which are expected to begin on Saturday.
A rally and march was held Saturday evening in downtown Chicago against the anticipated surge in ICE operations. A large crowd gathered at Michigan and Ida B. Wells before marching up Michigan Avenue.
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President Donald Trump says the surge in immigration enforcement activity in the Chicago area is about getting dangerous criminals off the streets.
The White House has not released any details about what's being planned. City and state leaders oppose deploying federal agents to the city.
Massive crowds march through downtown, criticize Trump administration
Protests wrapped up Saturday night in the city and suburbs as federal immigration enforcement was expected to expand. The protests stayed peaceful, but demonstrators had a strong message for the president.
Massive crowds marched through downtown Chicago. At least a few thousand people protested the Trump administration.
Many people expected to see DHS operations in the city this weekend, but that has not been the case so far, and the protestors said federal agents are not needed here.
Several organizations came together in downtown as they say now is the time to send a message to the administration.
"We have to stand up together and say very loudly and proudly that this is not gonna happen," said Kobi Guillory, co-chair of Coalition Against Trump. We are not accepting this."
The group remained peaceful as they marched down Michigan Avenue, chanting loudly while holding signs.
"99% of the people that are here that come to America and Chicago are hardworking," a protester named Kevin said. "They want a better life for their families."
Many of them said they're concerned for their neighbors and believe the president is targeting the wrong people.
"I myself am an immigrant, and it's very important for immigrants to be in this country," a protester named Barbara said. "They make this country great."
More protests continued north of Chicago as well with a group gathering near the Naval Station Great Lakes. Protesters there say more federal operations in Chicago may lead to problems for other states too.
It remained quiet Saturday night in Chicago. A fence remains up at the federal building downtown to allow access in and out of the building in case operations escalate in the coming days.
Trump social media post about Chicago draws criticism from Illinois officials
On Saturday, Trump re-shared an image that places him in front of Chicago in a post on his social media platform, Truth Social. His caption says, "'I love the smell of deportations in the morning...' Chicago is about to find out why it's called the Department of WAR."
While people raised their voices in the streets, federal and state leaders were sparring in a war of words. President Donald Trump posted an inflammatory message on social media Saturday referencing Chicago, and it prompted quick responses from Illinois Governor JB Pritzker and a U.S. senator.
Trump social media post about Chicago draws criticism from officials
Trump re-shared an image that places him in front of the Chicago skyline with the caption, "Chipocalypse Now."
Trump's caption said, "'I love the smell of deportations in the morning...' Chicago is about to find out why it's called the Department of WAR."
Trump's post comes as he has said he plans to send National Guard troops to Chicago and also follows him signing an executive order to rename the Department of Defense, the Department of War.
The president's post drew strong reaction from local and state democratic leaders, including Governor Pritzker.
Pritzker shared the president's post and responded on "X," saying "The President of the United States is threatening to go to war on an American city. This is not a joke. This is not normal. Donald Trump isn't a strongman, he's a scared man. Illinois won't be intimidated by a wannabe dictator."
Joining the governor in his criticism of the president was Illinois U.S. Senator Dick Durbin, who spent part of his Saturday in Pilsen for the Mexican Independence Day Parade.
"His tweet this morning was disgusting to suggest that the troops are coming into Chicago or that the Department of War is going to be engaged is an embarrassment," Durbin said. "This is a peace loving community trying to do their best to make a living and raise a family."
Fellow Illinois U.S. Senator Tammy Duckworth especially took issue with the image's depiction of the president, saying "Take off that Cavalry hat, you draft dodger. You didn't earn the right to wear it. Stolen valor at its worst."
Chicago Mayor Brandon Johnson also weighed in on "X," saying "The President's threats are beneath the honor of our nation, but the reality is that he wants to occupy our city and break our Constitution. We must defend our democracy from this authoritarianism by protecting each other and protecting Chicago from Donald Trump."
In a statement released to ABC News, the White House doubled down on President Trump's post, pointing to Labor Day weekend violence in the city of Chicago and saying, "Local democrat leaders are more upset about a post from the President - that tells you everything you need to know about the Democrats' twisted priorities."
The latest developments come after Sens. Durbin and Duckworth, along with Congressman Brad Schneider, went to the Navy directly for answers on Friday.
They say the admiral-in-charge at Naval Station Great Lakes told them that Immigration and Customs Enforcement and Department of Homeland Security officials requested office space and parking at the base from Sept. 5 through Oct. 5.
The Navy agreed, but is not providing barracks or housing, nor are they allowing the federal agents to have lethal munitions on base.
The Illinois representatives say they tried to speak with DHS officials on base, but with no luck.
Demonstrators could already be seen outside of a now-boarded up Broadview ICE facility on Friday. That facility is expected to be used as a processing center for operations every day for perhaps the next month-and-a-half.
Mexican Independence Day Parade held in Pilsen despite fear over ICE raids
Despite fear in some Chicago communities over the expected surge in immigration enforcement, Pilsen held its Mexican Independence Parade on Saturday. There were some extra precautions taken in case federal agents showed up.
This year's Pilsen Mexican independence Day Parade not only looked different, but felt different. A lot of the community and their supporters have concerns over the administration's continued immigration enforcement.
Pilsen Mexican Independence Day Parade held despite ICE raid concerns
"I just think we still need to be out here, and so we're not scared and still show our heritage, and that we're a proud people, and that we're not scared of anything that's going on," paradegoer Jasmine Martinez said.
For a 24th time, the annual procession headed across 18th Street at noon as heightened security concerns loomed following the Trump administration's threats to deploy National Guard troops and ICE agents to the city.
"I'm against goons and masked people, that's like the KKK," Pilsen resident Tom Sanchez said. "So, I'm here."
Bands, colorful floats and dancers marched in the parade to noticeably smaller crowds.
According to the most recent census, Chicago's Mexican-American community represents 21.5% of the city's total population. The threat of federal intervention has turned what is usually a time of celebration to one of anxiety in Latino neighborhoods.
"It does seem a little bit less crowded than the last time we were here," paradegoer Ben Snyder said.
While reports of ramped-up deportation efforts caused other celebrations to be canceled or postponed, organizers of Pilsen's parade said they did not think their event would be targeted, but still staged safety volunteers armed with warning whistles along the short parade route as a precaution.
"Three continuous whistles, like this, will mean an ICE sighting," said Vicky Lugo, parade organizer and Pilsen Chamber of Commerce board member. "A continuous whistle like this [means someone is getting arrested by immigration agents.]"
Some of Illinois' elected official have rejected Trump's plans.
"This is more than a parade today, this is a show of unity," Congressman Mike Quigley said. "This is a reminder that there is more than unites us than divides us."
The actual Mexican Independence Day falls on September 16, but celebrations will continue throughout the week, usually drawing hundreds of thousands of people. Where there were no issues at Pilsen's parade this year, there are concerns about next weekend. That's when the Little Village Mexican Independence Day Parade kicks off. There's concern there could be some enforcement activity there.
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Meanwhile, suburban communities are also taking precautions ahead of the anticipated surge in immigration enforcement.
Wauconda is canceling its Latin Heritage Fest. Organizers say they know how meaningful the event is for the community, but they say safety needs to come first.
In Aurora, Fiestas Patrias is still on for this weekend. The city's special events team said it is working closely with public safety departments to make sure it is safe for everyone.
Chicago educators are launching a new campaign to get information out to families as these operations begin.
A group of Chicago Public Schools teachers has been distributing so-called "defend your rights" flyers at schools across the city.
The Chicago Teachers Union says it will also activate teams to have a watchful presence around their schools.
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