Police said the crash happened in the Roscoe Village neighborhood near West Addison Street and North Western Avenue just after 3:20 a.m.
Police said a black Honda sedan, traveling eastbound on Addison Street, sped through a red light and hit a white Toyota SUV, which was facing southbound on Western Avenue.
The impact caused the Toyota SUV to flip upside down and hit a light pole, police said. The Honda sedan's driver lost control and hit a black Toyota sedan, which was facing northbound on Western Avenue.
The Honda sedan's driver, a 21-year-old man, and two passengers, a woman and a 22-year-old man, were hospitalized in critical condition. All three suffered head injuries.
The Toyota SUV's driver, a 57-year-old man, and his passenger, a 37-year-old man, were hospitalized in fair condition. Both suffered cuts to the head.
The Toyota sedan's driver, a 41-year-old woman, was hospitalized for evaluation.
Citations are pending, and CPD's Major Accidents Unit is investigating.
CPD did not immediately provide further information about the crash.