Dewayne Chester

Dewayne Chester, a 33-year-old man, was shot and killed in Chicago on the evening of Wednesday, November 4, 2026. His death is one of many unsolved homicides in a city that has long grappled with gun violence. Details about Dewayne's personal life, including his family, work, and what brought him to the park that day, have not been shared publicly.

The fatal encounter occurred at approximately 6:22 p.m. in Ellis Park, located in the 3500 block of South Vincennes Avenue in the city's Oakland neighborhood on the South Side. As evening fell over the park, Dewayne was struck in the neck by gunfire. According to the Cook County medical examiner’s office, he suffered multiple gunshot wounds. Police and paramedics responded to the scene, but his injuries were too severe, and he was pronounced dead right there in the park.

The Chicago Police Department is handling the investigation. In the immediate aftermath of the shooting, authorities stated that no one was in custody, and they had not publicly identified any suspects or a possible motive for the attack. The circumstances leading up to the shooting remain unclear, and police have not released any descriptions of potential offenders or whether Dewayne was with anyone at the time. The case remains open, pending further investigation by Area One detectives.

This was not Dewayne Chester's first encounter with the criminal justice system. More than a decade earlier, in February 2013, a 20-year-old Dewayne was charged with first-degree murder for his role in the June 24, 2012, shooting death of 13-year-old Tyquan Tyler in the West Woodlawn neighborhood. Prosecutors alleged that Dewayne was a member of a faction of the Gangster Disciples and had been involved in a dispute with a rival gang.

According to authorities at the time, Dewayne was with another man, Nasean Flowers, when Flowers fired into a group of people in an alley, striking Tyquan in the chest. Prosecutors said Dewayne admitted to being with Flowers, seeing the gun, discussing the best vantage point for the shooting, and fleeing the scene afterward. He was initially held on a $750,000 bond.

Ultimately, Dewayne Chester pleaded guilty to a lesser charge of conspiracy in connection with Tyquan's death and testified at Flowers' trial. He was subsequently sentenced to seven years in prison. His co-defendant, Nasean Flowers, was convicted of murder and sentenced to 55 years in prison in December 2015. After serving his sentence, Dewayne was released, years before he would be killed himself.

As of November 2026, no arrests have been made in Dewayne Chester's homicide. Investigators are still seeking information from the public to help solve the case. No reward has been announced, and no vigils or memorials have been publicly reported. The Chicago Police Department urges anyone with information to come forward.