Police say the man had a weapon and confronted them. Three officers were also transported to the hospital in good condition for minor injuries.
The incident happened around 6:30 p.m. Sunday near Grand Crossing Park at 76th and Ingleside.
Police say they recovered the injured man's weapon at the scene.
The park was filled with families celebrating Father's Day at the time of the incident.
"I saw a guy going through the park. He ran over by the trees, and he looked like he had a pistol. After that, the police started coming from every direction. After that, we heard about 14 shots, just pop, pop. I don't know if he shot back at the cops," witness Marion Jeffery said.
The man was rushed to Stroger Hospital, where he was listed in critical condition.