Police said the victim was stabbed in the neck and stomach after he declined to give the alleged attacker a cigarette near the Metropolitan Correctional Center at the intersection of West Van Buren Street and Clark Street around 8:40 p.m.
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The suspect fled in an unknown direction, police said. Officials said the victim walked a short distance before others found and helped him.
"I always took this street home to go to the train so it's just like knowing that this happened here is scary," said Kristin Chestnut.
"The Correctional Center is like right here so I would think that it would be pretty well lit and and watched and stuff so for something like that to happen is frightening," said Clarissa Dominguez.
The victim was taken to Northwestern Memorial Hospital in serious to critical condition, officials said.
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The suspect is described as a black man between the ages of 38 and 45 and approximately 6'2" tall. Police said he was wearing light blue jeans with a name tag hanging from the pocket.
Violent crime in the downtown area has prompted businesses to add armed security in the Loop. In March, the Chicago Loop Alliance announced plans to pay for armed guards to patrol the State Street corridor.
A few weeks ago in South Loop, robbers were caught on security cameras as they escaped on the L after the grabbed, punched and threw their victims to the ground before stealing their belongings. In a separate incident, a CEO was stabbed in the neck in River North.
Area Central detectives are investigating.