Following the first or last leg of Route 66 across Chicago and its hinterlands is really not worth the effort for anyone except the most die-hard end-to-ender—even Jack Rittenhouse, in his original 1946 Guide Book to Highway 66, didn’t bother to describe the route until it reached Plainfield, 35 miles southwest of the Loop. For a symbolic end point, you can use the grand old Art Institute of Chicago in Grant Park along the lakeshore, since the last US-66 shield used to hang from a streetlight just south of the gallery. If Chicago is your “end of the road,” you’ll probably prefer to avoid the final few miles of surface streets and make your way to town as quickly as possible via I-55. Starting from Chicago, as the song says you should, you may be more willing to take the time to see what’s left of the Mother Road.
From Lake Michigan, the old road ran west via Adams Street (take Jackson Boulevard eastbound; both are one-way) before angling southwest along Ogden Avenue—a long, diagonal exception to the city’s main grid of streets. Near Cicero, which prides itself on having been a haven to Al Capone and other mobsters during the Prohibition era, there’s one oddity worth checking out: “The Spindle,” a tower of ruined cars impaled on a 50-foot steel spike, standing in the parking lot of a shopping mall at the corner of Cermak Road and Harlem Avenue, two miles north of old Route 66. (You may have seen The Spindle in the 1990s comedy Wayne’s World.)
To continue south and west, you have to follow I-55, which was built right on top of old Route 66. In Willowbrook, off Hwy-83 on the north side of I-55 just a dozen miles from the Loop, Dell Rhea’s Chicken Basket (630/325-0780) at 645 Joliet Road is a welcoming old roadside tavern, with famously fabulous chicken dinners and frequent live music.
Further west, Route 66 crossed the old Lincoln Highway (US-30) in suburban Plainfield, then followed the Des Plaines River and the Chicago Ship and Sanitary Canal as far as Joliet, where Route 66 resurfaces again.
Chicago marks the junction of Route 66 and our cross-country route along The Oregon Trail.
