Chicago police said the victims were approached by a group of unknown men near the 3200 Block of W. Congress. At least one person in the group fired shots at the two men, striking them both.
The 33-year-old man suffered a gunshot wound to the chest and he was pronounced dead at a nearby hospital.
The 41-year-old man is hospitalized but in good condition.
No individuals are in custody at this time.
Detectives are investigating the shooting.