President Trump vowed to send federal troops to Chicago after a bloody weekend of violence left 63 shot and 12 people killed, including two children.
Tensions between Trump and the mayor of Chicago erupted after he tweeted about the ongoing violence in her city.
Trump vowed to send federal troops to the Democratic stronghold this week to quell the violence.
"How about Chicago? Would you say they need help after this weekend?" Trump told reporters at the White House on Monday. "You know the numbers that you hear, the numbers? Many, many shot. Many, many killed."
Mayor Lori Lightfoot said she had concerns about federal troops who disrupted Antifa and Black Lives Matter uprisings in Portland, Oregon over the weekend.
"I have great concerns about that in particular, given the track record in the city of Portland," Mayor Lightfoot said.
Federal agents in unmarked cars ambushed startled protestors in Portland and took them to unknown locations over the weekend.
Unlike the National Guard, federal agents have more powers to arrest and detain people who trespass or commit crimes on federal property.
"I have talked to the mayor of Portland (and) we don't need federal agents without any insignia taking people off the street and holding them, I think, unlawfully," Lightfoot added.
At least 18 Chicago police officers were hospitalized after hundreds of protesters - many holding black umbrellas to shield their identities, assaulted police with frozen water bottles, rocks, and other projectiles as they tried to take down the statue of Christopher Columbus in Grant Park on Friday.
Mayor Lightfoot blamed "a group of vigilantes" who came to Chicago "for a fight, not a peaceful protest."