An investigation is ongoing, but police said it was not a random shooting and the two men hit by gunfire were targeted.
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Police said the shooting happened around 4 p.m. on the elevated Argyle Station platform.
A 34-year-old man was shot in the back, belly, buttocks and groin, and taken to St. Francis Hospital in critical condition, police said. A second man suffered a graze wound to his thigh and declined medical treatment at the scene, police said.
Chicago police said the area around the shooting is heavily saturated in high definition crime cameras and detectives are currently reviewing digital evidence.
Police said they're searching for one gunman.
"We do feel that this was a specifically targeted. These two individuals are known to police. They were targeted," said Sgt. Rocco Alioto. "We have a lot of high definition video as well as physical evidence which detectives will be poring over"
People who work nearby said people at the station ran after hearing the gunfire. Witnesses heard several shots.
"Minimum of 10 shots or more," said Bin Chen, who works nearby. "It's scary. We see a lot of people running down the block, running to the store, hiding."
The area is bustling with cafes and restaurants, and popular with pedestrians.
"I couldn't see the gunman, but I did see someone stick what looked like a gun in their pocket and take off running," said Gustavo Benites, who works nearby.
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CTA trains resumed making stops at the Argyle station after 7:30 p.m.