Chicago police and fire officials said the crash took place just after 10:15 a.m. on 31st Street and Kedzie Avenue in the Little Village neighborhood.
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The driver of the bus and the other car involved were taken to Mount Sinai Hospital in serious-to-critical condition.
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The nine students with special needs, ages 16 to 18, were taken to Stroger and Saint Anthony hospitals in good condition.
Five adults on the bus were also taken for medical care.
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Chicago police said a man driving an SUV was traveling south on Kedzie, when he tried to pass a semitrailer that was also traveling south. The SUV went into oncoming traffic, and hit the northbound bus.
The driver of the SUV was cited for operating an uninsured motor vehicle and driving on a revoked license.