Route 66, the quintessential American road trip, spans 2,500 miles across eight states from Chicago to Santa Monica. With 2026 marking its 100th birthday, this year is the perfect time to explore this cultural icon. Here is a guide to an authentic Route 66 experience, from the best breakfast spot in Chicago to the rituals at the finish line.
Commissioned in 1926 and fully paved by the late 1930s, Route 66 stretched 2,448 miles through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. It gained legendary status after John Steinbeck dubbed it the 'Mother Road' in his 1939 novel The Grapes of Wrath, which chronicled the migration of farmers to California. After the Second World War, car ownership surged, and Americans embraced the road for its desert landscapes, neon-lit motels, and diners. Decommissioned in 1985, it was replaced by the Interstate Highway System but remained ingrained in popular culture through songs like Bobby Troup's '(Get Your Kicks on) Route 66' and countless films.
The traditional starting point is in downtown Chicago on Adams Street, near the Art Institute of Chicago, where a brown-and-white 'Begin Route 66' sign marks the spot. Before setting off, tradition dictates a breakfast at Lou Mitchell's restaurant on W. Jackson Boulevard, serving classic diner fare since 1923. While waiting, staff hand out complimentary donut holes and Milk Duds. A recommended stay is the Silversmith Hotel Chicago Downtown, a three-minute walk from the route, offering rooms with mini-refrigerators, coffee makers, and wifi.
Navigation requires caution: Google Maps is unreliable as Route 66 is no longer a single continuous highway but a patchwork of historic sections interspersed with modern interstates. Following 'Historic Route 66' signs is essential to avoid missing fascinating roadside attractions. The journey is best savoured over two weeks, allowing time to explore the eccentric sights and classic motels that evoke the 'good old days'. The trip culminates at Santa Monica Pier, where rituals mark the end of a road trip of a lifetime.
