Old Joliet Prison, Illinois Wine Country & a Classic Diner

Old Joliet Prison is the most underrated day trip from Chicago. The Romanesque castle-style prison operated from 1858 to 2002 — John Dillinger, Leopold and Loeb, and Richard Speck all passed through its 40-foot limestone walls, and the opening scene of The Blues Brothers was filmed here in 1979. Guided tours run through original cellblocks, the stone quarry, and the restored dining hall on weekends. Sable Creek Winery in Channahon opens the morning 46 minutes southwest of Chicago, and Merichka's in Crest Hill — legendary broasted chicken, cash only, operating since 1933 — closes it out before the hour drive home.