The shooting happened just before midnight in the 2500-block of North Lake Shore Drive. Police said the victims told officers they were driving in a Honda Odyssey going northbound on Lake Shore Drive near the Fullerton exit when a vehicle drove up alongside them and fired multiple shots.
Police said the shooters took off as the victims exited on Belmont and drove to a Walgreens parking lot, where ambulances transported the surviving victims to nearby hospitals.
Ahmad Hajhassan was nearby when first responders filled the intersection and caught some of the commotion on camera.
"i never thought in a million years I'd run into that in my neighborhood," Hajhassan said.
Hajhassan said he could hear one man yell, "I've been shot, please be careful with me," as police removed him from the bullet riddled van. He said police then smashed out one of the vehicle's windows.
"Maybe just to have visibility as to what was going on internally inside the van," Hajhassan explained.
Michael Medina, 20, was shot in the chest and pronounced dead at the scene.
Another 20-year-old man was shot in the shoulder and a 26-year-old man was shot in the head and torso. Both were transported to Illinois Masonic Medical Center in critical condition. A fourth man, 22, was shot in the arm, chest and face, and transported to Northwestern Memorial Hospital in critical condition.
"[One man] immediately just kind of fell on the floor right here on the corner." Hajhassan said. "You could see the bullet wound on his shoulder."
Friday night police held a roll call in Lake Shore Park.
Second Ward Alderman Brian Hopkins said he is well aware of escalating crime, and some of his residents are frustrated.
"Even as we are having this rollcall meeting there was a shooting less than a mile from here and an armed robbery in this neighborhood just in the last 45 minutes," Hopkins said.
"I don't drive at night, I'm fearful of that, and I'm also hesitant to walk to the park and the things that I used to do freely," said resident Angela Griffin.
In Streetrville Chicago police were joined by Northwestern University Police, who are also concerned about an uptick of violence near their downtown campus.
Other neighbors in the Lakeview area said this type of scene is uncommon.
"I actually had a friend reach out to me and she was like 'is everything ok,'" said Lakeview East resident Natalie Gower. "You just kind of think this is a safe area, so when you hear about things like that it's very unsettling."
"This area has a lot of kids, I mean this is a big family area and we have a great school which is right up there, just right up there a half block up," said Lakeview resident Chris Collins.
"I am shaking a little bit now because it's just really odd for me to hear," said Lakeview resident Felix Amankona-Diawuo. "I didn't know there was anything sort of like that going on in this neighborhood, so that's really unfortunate."
The local Chamber of Commerce stressed the neighborhood is safe and called on the mayor and police department to accelerate their plans for reducing violence.
"This is a city-wide problem that we're seeing with gang activity and I think resources need to come from a number of places to help us," said Lakeview East Chamber of Commerce Executive Director Maureen Martino.
Martino said she wants police to add patrols, and said her organization already planned to do so with its private armed security team because the weather is warming up.
Still, Martino stressed the shooting didn't happen in her neighborhood and said it's still a "very safe" area.
Small business owner Dan Kanellakis, who's owned Broadway Shoe Repair for 29 years, called the shooting "a fluke."
"This has always been the safe neighborhood to walk in... and it isn't any longer," said longtime resident Gayle Tepper, who has lived in Lakeview East for 11 years.
No one is in custody and investigators believe the incident may have been a targeted shooting.
Chicago Police Department spokesman Anthony Guglielmi said, "We know this was a targeted shooting based on the victim profiles and a historical gang conflict." He added that there was a marked CPD car, with lights flashing, on Lake Shore Drive roughly one block south of where the shooting occurred.
Police are asking anyone who may have seen erratic driving on Lake Shore Drive overnight to please come forward with information.
In total, at least 13 people were shot across the city since Thursday evening.