A few country songs refering to Chicago or Illinois...
North To Chicago - Hank Snow When The Wind Blows In Chicago - Roy Clark I Hate Chicago - Mark Wills The Airport In Chicago - Bobby Bare Great Chicago Fire - Faron Young O'leary's Cow - Johnny Horton The Cold Windy City Of Chicago - Boxcar Willie The City Of New Orleans - Willie Nelson Backing To Birmingham - Flatt & Scruggs If Texas Told What Arkansas - What Did Tennessee? - Lonzo & Oscar