Chicago Police Department spokesman Anthony Guglielmi said police suspect the man, a well-known gang member with an extensive criminal history, was the target of the shooting that also left a woman wounded.
The toddler is the second child to be killed in Chicago in a matter of days following the shooting of 11-year-old Takiya Holmes, who was hit in the head by a stray bullet inside her home in the city's South Side on 11 February. She recorded the incident as it unfolded on Facebook Live, unaware that they would be ambushed on their drive as the couple sang along to a Chief Keef song.
A second vehicle drove by with three people inside. Her boyfriend was driving and the toddler, identified as Lavontay White Jr., was sitting in the backseat.
Police said Lavontay White Jr. was shot in the head while sitting in the back of a auto.
Ms Devonte runs back down the street and begs a neighbour to let her in. At one point she can be heard screaming to an onlooker: "Call 911!" "I can't go to the hospital ... this bullet in my stomach". "Oh my God, Lord, please".
The woman's boyfriend and nephew were both shot in the head. The man, who was in the passenger seat in front of the child also died at the scene, while the aunt, who is pregnant, was shot in the stomach. No one is in custody.
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"We have very promising leads; we have video", Johnson said.
"My gut is telling me that when we finally find this guy, we're going to find that he's a repeat gun offender".
In the North Lawndale area, a 15-year-old boy suffered a graze wound to the leg in the 4300 block of West Ogden Avenue about 5:35 p.m., according to a police media notification. We have yet another innocent child in Chicago that can lose their life over senseless gun violence.
"This has got to stop", Johnson said at the crime scene.
Chicago Mayor Rahm Emanuel released a statement to say that when children are killed "our consciences are shaken and are hearts are broken".
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