The shooting occurred in the outbound lanes of the Dan Ryan Expressway at about 2:09 a.m. near Garfield Boulevard.
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The Chicago Fire Department said a 39-year-old man was transported to the University of Chicago Medical Center with a gunshot wound to the head.
The fire department said two women, ages 27 and 20, were both transported to St. bernard Hosptal in good condition with injuries from the crash.
Illinois State Police are investigating.