Joliet police spotted a gray Honda driving the wrong way west in the 500-block of West Jefferson Street, near the Will County Courthouse, about 9:30 p.m. on Memorial Day.
An officer tried to stop the car, but it continued west over the Jefferson Street Bridge, police said.
It passed North Hickory Street and Center Street before crashing into a black Chevy Equinox, police said.
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Joliet Fire Department paramedics took both drivers to Saint Joseph Medical Center in critical condition. They remained stable, police said.
Jefferson Street was closed from Wilcox Street to Nicholson Street for an investigation.
Anyone with information on the crash is asked to call Joliet police at 815-724-3010.
Contact Will County Crime Stoppers at 800-323-6734 or submit a tip online at crimestoppersofwillcounty.org to remain anonymous.