The shooting happened just before 4:40 p.m. near 70 E. Oak St., police said.
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East Oak Street is typically known for some of Chicago's most expensive shopping, but it turned into a crime scene Tuesday, rattled by gunfire and littered with bullet casings.
Three people were shopping on Oak Street when two vehicles pulled up. Four people exited those vehicles and shot at the shoppers on the sidewalk, police said.
"The offenders then produced firearms and fired shots at all three victims," police said in a statement Tuesday evening.
The shooters fled the scene by car, police said.
A 26-year-old was shot in the chest, the groin and the neck. He was transported to Northwestern Hospital where he was pronounced dead just after 5 p.m., police said.
Multiple friends and people who know the deceased man identified him as Chicago rapper FBG Duck.
The Cook County Medical Examiner's Office identified him as Carlton Weekly of Markham.
A woman, 28, was shot in the hand and taken to St.Joseph Hospital where she was in stable condition.
A 36-year-old man is in serious condition at Northwestern Hospital after he was shot in the back and side.
"One guy pulled out a gun and start shooting at the other guy close range; after they stopped shooting, the guy who was doing the shooting ran that way," a witness said.
Chicago community activist Ja'Mal Green said several people called him about the shooting. He was told FBG Duck was shopping with friends when someone fired shots at them.
Police said they were standing on the sidewalk near the Dolce and Gabbana store, just a few steps from Michigan Avenue.
Green described the 26-year-old as a well-respected, well-loved rapper but also as a well-hated one in the music world.
A lot of young people looked up to him and liked his music, Green said. They will need help coping with the loss.
"I was standing here and saw people running in every direction trying to look for cover," local business owner Howard Gordon said. "I was standing where we are standing now, and heard what I thought was a machine gun, and then a black car speeding down Oak Street going west."
Business owner Barbara Gordon said she counted about 17 shots.
Shoppers and residents scrambled as the two men dropped to the ground from the stream of bullets.
Police recovered one weapon from the scene.
The shooting is under investigation.
Police have asked people to avoid the area as they investigate. They are working to recover video from the nearby stores and seeking out witnesses.
Anyone with information is asked to submit an anonymous tip at cpdtip.com.