The Windy City had long served as a major waystation for shipping goods west when Route 66 was commissioned. See the official start sign at the intersection of S. Michigan Ave. and E. Adams St., across from the Art Institute of Chicago. Grab a meal at Lou Mitchell’s, family owned since its founding in 1923. Stand on the Ledge at Skydeck Chicago, which rises 103 floors and 1,353 feet over the city giving visitors views over four states on clear days. Also occasionally vertigo.