Dierks Bentley will hold his next Miles & Music for Kids event in Chicago on Oct. 9 with proceeds benefiting the city's Children's Memorial Hospital. Bentley and participating motorcycle riders will depart from the Fox River Harley-Davidson in St. Charles, Ill., with a street festival outside Joe's Bar after the 90-minute ride. Concert guests include Eli Young Band, Jerrod Niemann and more. Tickets go on sale Friday (Aug. 26). Over the event's six-year history, Bentley has raised more than $1.6 million for Children's Miracle Network hospitals. The events are co-sponsored by CMT One Country and Nationwide Insurance.