The shooting occurred just after midnight in the 1100-block of South Des Plaines Street, police said.
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One victim, a man in his 40s, was shot in the torso and transported to Stroger Hospital in critical condition, where he later died, police said.
The second victim, a 32-year-old man, was shot in the head and transported to Stroger Hospital in fair condition, police said.
Video from the scene shows police investigating near a homeless encampment.
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Area Three detectives are investigating and no one is in custody.
The shooting came after a violent 4th of July in Chicago, with 20 people shot, two fatally, on Tuesday, police said.
OEMC, Chicago police and OEMC plan to hold a news conference Wednesday afternoon to discuss safety efforts over the 4th of July holiday.
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