The crash happened near Westpoint Toll Plaza at mile marker 1 after a Lake County (Indiana) police pursuit, authorities said.
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After police attempted to safely stop the vehicle, it crossed over into the eastbound lanes and hit another car head-on, police said.
The car being pursued was stolen from Chicago and driven by a 20-year-old man from Waukegan, police said. He sustained life-threatening injuries in the crash and was taken to a hospital.
The other vehicle involved in the crash was occupied by a family of four who were all treated for injuries at the scene and taken to a hospital for observation.
Chopper 7 was over the crash at 3:30 p.m., and all eastbound lanes appeared to have been closed as police investigated the scene.
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No further details about the police pursuit were immediately available. Charges were pending.
The eastbound lanes were reopened on the Indiana Toll Road after 5 p.m.