Police said preliminary information suggests the three were in the 2300-block of West 55th Street just after 9 p.m., when the teen and a 39-year-old man began exchanging gunfire with a 27-year-old man.
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The 27-year-old was shot multiple times and taken to Advocate Christ Medical Center in Oak Lawn in good condition, police said.
The 14-year-old boy was shot in the torso and shoulder, and was taken to Comer Children's Hospital in critical condition.
SEE ALSO: Man dead after being shot while driving, crashing into parked cars in Calumet Heights, police say
The 39-year-old man was shot in the wrist, and taken to Mt. Sinai Hospital in fair condition.
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The 27-year-old said someone in a blue van shot at him, police said.
No one was in custody early Friday morning.
Area One Detectives are investigating.
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