"Seven people shot and killed yesterday in Chicago. What is going on there -- totally out of control. Chicago needs help!" Trump wrote on Thursday.
As officials take measures to curb the violence on the streets, the bloodshed has brought trauma to the lives of thousands of people in the city. Here's a snapshot of the violence that erupted on Wednesday.
Police on Chicago's South Side responded to a call from a family member of an unresponsive 60-year-old man who was bleeding on the floor of his home garage. He was transported to Mount Sinai Hospital, where he was pronounced dead from gunshot wounds to the back, neck and mouth, police said. The investigation is ongoing; no one is in custody.
7:35 p.m.: 900 block East 133rd St.
Police found a 44-year-old man bleeding from a gunshot wound to the head. The victim was pronounced dead at the scene, police said. No one is in custody.
8:15 p.m.: 7600 block of South Champlain Ave.
Wilteeah Jones, her unborn baby and her boyfriend were killed on the South Side, police said. Jones' 20-year-old boyfriend was fatally shot in the neck while sitting in the driver's seat of a parked vehicle, police said. Jones' body was found with gunshot wounds to the abdomen and side on a sidewalk, police said. It is unknown how far along in the pregnancy Jones was. The couple was transported to Stroger Hospital, where they were pronounced dead.
8:35 p.m.: 11400 block of South Ada St.
A 31-year-old man was pronounced dead on the scene of the shooting in the city's South Side after he was fatally shot in the head and back. Police said a person of interest is being questioned.
8:50 p.m.: 9100 block of South Emerald St.
A 24-year-old man was standing on the sidewalk when an occupant in a dark-colored sedan fired shots. The victim was transported to Christ Hospital, where he was pronounced dead from wounds to his head and back. No one is in custody, police said.
Trump vocal on Chicago violence
As President-elect, Trump encouraged Mayor Rahm Emanuel to ask for federal assistance.
Emanuel said he "welcomed" the idea of greater federal assistance to address crime in the city following Trump's comments.
Shortly after taking office in January, Trump tweeted about the shootings in Chicago again: "I will send in the Feds," he wrote, if they don't fix the "horrible carnage" going on.
Emanuel said federal authorities already play an integral role in fighting crime in the city, referencing the transport of guns across state lines, among other areas.
"A lot of the guns, you know, coming into Chicago come from out of state," Emanuel said. "Federal entities are set up to deal with that. And they do. And they work with us."
Previously, Emanuel has specified areas he'd like the federal government's help -- including gun control, gun tracking, prosecution for gun crimes and help increase funding for more police officers.
Although Chicago does have strict gun laws, 60% of the guns used in shootings were purchased out of state.
Illinois Gov. Bruce Rauner recently signed a new gun control law that imposes harsher penalties on those who bring in guns from out of state to sell and do not have gun-owner ID cards.
Last year marked the deadliest year the city has seen in nearly two decades, with a reported 762 homicides.
Chicago has had 91 homicides so far this year, compared to 93 for the same period of 2016.
The number of shootings as of Friday stands at 382 - compared to 371 at the same time last year, police said.