The 62-year-old victim was riding his bicycle on the sidewalk in the 2200-block of South State Street at about 1 a.m. when witnesses told police someone started hitting him with a construction sign.
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The attacker then grabbed the victim's bicycle and started beating him with that, police said.
A witness said paramedics arrived and started giving the 62-year-old man CPR. The critically injured victim was rushed to Northwestern Memorial Hospital, police said.
Mark Anderson lives near State Street and Cermak Road where it happened, saying he's disturbed by this level of violence.
"I'm saddened but I have hope," Anderson said. "I'm full of hope. I'm sad when I hear anybody being a victim of unnecessary acts of violence. There's no need for that man to be treated the way he was treated."
Maureen Battiste commutes to work through this area of the South Loop and said she constantly feels on edge.
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"Every time I come through here," Battiste. "It's OK during the daytime but it's like once the sun goes down, I make sure not to get caught around here."
The motive behind the attack is unclear, but it has left many concerned for their safety.
"It doesn't take much to set a person off," Battiste said. "Your don't even have to say anything. Must look at 'em wrong...it doesn't take much for us to turn on each other."
No one is in custody and Area Five detectives are investigating.