Police said the crash happened in the Lincoln Park neighborhood's 2000-block of North Halsted Street just after 3 a.m.
A black sedan, heading northbound on Halsted, collided with another black sedan in the intersection, police said.
All five people inside one of the vehicles suffered various injuries and were taken to local hospitals for treatment.
Both people inside the other sedan suffered minor injuries. They were taken to a local hospital.
Citations are pending and the crash is under investigation, police said.
Police did not immediately provide further information about the crash.