Farah, who had spent the week fending off questions about his former coach Alberto Salazar, was already a minute behind when the leaders hit the halfway mark in Illinois and it soon became a four-way fight for the title. He only just broke the 2:10.00 mark, coming home in eighth.
His training partner Bashir Abdi stayed with him in an effort to pull him back into contention but he was not in the required shape to compete.
Cherono had won the Boston Marathon back in April in a time of just under two hours and eight minutes but has a personal best of 2:04.06 and was within two minutes of that time, winning in a time of 2:05.45.
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"The race was very competitive from the beginning," Cherono said.
"We had strong pace-makers and after they went we had to struggle on our own from 30 kilometres and from 40 kilometres it was anybody's race.
"But at 41 kilometres I saw everyone was not going again so I decided to kick again and my luck was in."
Dejene Debala, the Ethiopian who had kicked two kilometres from home in an effort to go one better than the second he achieved in Paris, was forced to be happy with the second spot on the podium once again, just a second behind the winner.
His countryman Asefa Mengstu came in third while Bedan Faroki, the final member of the leading group, came in fourth.
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