Chicago police said someone in a white truck fired shots at the men as they drove in the 1500 block of W. Wilson Ave just after 5 p.m.
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After being shot, the driver lost control and crashed into a fixed object and the vehicle caught fire, police said. He was pronounced dead on the scene.
Police said a 28-year-old male passenger was also shot in the chest. He was rushed to Advocate Illinois Masonic Medical Center in "grave" condition and later died there.
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The victims have not yet been identified. So far, no one is in custody.