The crash occurred at about 3:49 a.m. in the 1100-block of North Lake Shore Drive near the Oak Street curve. Lanes were shut down with traffic diverted before reopening after 7:30 a.m.
Police said a driver was going southbound in the northbound lanes and struck a car driving northbound.
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Two women in the vehicle going the wrong way were transported to Northwestern memorial Hospital in critical condition, police said.
A man in the vehicle that was hit was transported to Northwestern Memorial Hospital in good condition.
Citations for the crash are pending, police said.