According to authorities, the guys were involved in a fight with another individual in the 200 block of South Wabash Avenue when they were shot.
A shooting that happened early on Sunday in the Loop badly injured two guys.
Around 12:05 a.m., the gunman pulled out a revolver and fired four shots at them and another man as they quarrelled outside the 2Twenty2 Tavern bar in the 200 block of South Wabash Avenue, according to Chicago police and a witness there.
The shooter and a woman wearing all pink clothing were last seen travelling south on Wabash.
The 40-year-old man was shot in the back and shoulder and rushed to Northwestern Memorial Hospital, where his condition was described as critical, according to police.
The second victim, a 37-year-old man, was shot in the chest and taken to Stroger Hospital, where his condition was rated as critical, according to police.
No one was detained. Detectives are looking into it.