Joliet (pop. 148,099), the “City of Steel and Stone,” has a rough reputation that dates back long before the 1970s, when Saturday Night Live star John Belushi sang in the Blues Brothers band as paroled convict “Joliet Jake.” Route 66 through this once-mighty industrial enclave is a feast for fans of postindustrial scenery. Along the Des Plaines River north of downtown is the now closed state prison from which “Joliet Jake” is released at the beginning of the 1980 movie that was filmed on location here and in Chicago.
Stalwart bridges cross the Des Plaines River and historic Illinois & Michigan Canal, which, beginning in the 1840s, connected Chicago with the Mississippi River before being replaced by the less salubrious Sanitary and Ship Canal. Old warehouse and commercial buildings survive all over town. The most notable is the lovely Rialto Theater on Chicago Street, where you’ll also find the original home of fast-food megacorp Dairy Queen. It’s now an official landmark—but it’s occupied by Paisano Auto Insurance (501 N. Chicago St.).
While the suburbs grow and grow, efforts to reverse downtown Joliet’s long economic downturn by embracing casino gambling have not had much success. The large Harrah’s Joliet Casino (151 N. Joliet St., 815/740-7800) draws gamblers but has not done much to revive the waterfront or the surrounding streets.
South of Joliet, following old Route 66 (Hwy-53) across I-80 brings you past the massive Chicagoland Speedway and the Route 66 Raceway (888/629-7223), where NHRA drag races, NASCAR stock car races, and occasional pop music concerts are held.