Investigators said a 52-year-old man was walking in the 2000-block of South Washtenaw Avenue about 5:10 a.m., and a man got out of a white car, pointed a gun at him, demanded money and took off.
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Ten minutes later, police said two robbers held up another 37-year-old man at gunpoint in the 2300-block of West 25th Street.
They drove off in a silver car heading north on Western Avenue.
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No one was hurt in either robbery.
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Chicago police have not said if the incidents, which happened about a mile apart, are linked.
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