The shooting took place just before before 12 a.m. in the 400-block of North Central Avenue in the Austin neighborhood.
Chicago polce police arrived at the scene and found two victims on the sidewalk.
A 17-year-old male was shot in the head and died at the scene. The other victim, an 18-year-old male, was shot in the chest and was in stable condition at Mt. Sinai Hospital.
Chicago police say they are investigating.
There were no arrests later Saturday morning.
The Memorial Day holiday weekend got off to a violent start in other parts of the city, as well. A 22-year-old man was shot in the head and killed in the Humboldt Park neighborhood in what police say was a gang-related incident. Also, three people were hurt in a drive-by shooting in that same area.
In Hyde Park, a 29-year-old man was shot fatally. Police said the shooting was gang related.
Lastly, one person was injured in a shooting in Chicago's Logan Square neighborhood.