Route 66 Tour Chicago to Santa Monica: 15 Days End to End

Make your own way from O'Hare to the hotel in the Loop, about 45 minutes by taxi or by the Blue Line train. Ray Lindqvist, your road captain, meets the group in the lobby at 6 pm. He grew up in Joliet, 40 miles down the road, and has driven the full route more times than he admits. A five-minute walk brings you to the brown Begin Route 66 sign on Adams Street, the first photo of the trip, before the welcome dinner at a Loop steakhouse.

Breakfast at Lou Mitchell's on Jackson Boulevard, open since 1923, where the servers still hand out Milk Duds. Then out through Cicero and Berwyn to Joliet and the Gemini Giant in Wilmington, a fiberglass astronaut nearly 30 feet tall. Afternoon stops at Ambler's Texaco in Dwight and the little 1932 Standard station in Odell, then the Illinois Route 66 Hall of Fame and Museum in Pontiac. About 210 miles and 8 hours with stops. The Cozy Dog Drive In, open since 1949, is a short ride from the hotel.

A morning in Springfield: the Lincoln Home, the only house Abraham Lincoln ever owned, and the Old State Capitol where he gave the House Divided speech in 1858. Lunch at the Ariston Cafe in Litchfield, in business since 1924. Then you cross the Mississippi on foot over the Chain of Rocks Bridge, a mile long with a 22-degree bend in the middle, while the coach waits on the Missouri side. End at Ted Drewes on Chippewa Street for a concrete, frozen custard thick enough to serve upside down. About 110 miles.

Southwest out of St. Louis to Meramec Caverns at Stanton, whose name was painted on barn roofs across the Midwest for decades, and an hour underground. Coffee in Cuba among the town's building murals, with a look at the stone cottages of the 1936 Wagon Wheel Motel. After lunch the old road drops to Devils Elbow, where a 1923 steel truss bridge crosses the Big Piney River below wooded bluffs. Tonight is the Munger Moss Motel in Lebanon, with its neon sign facing the old road. About 180 miles.

The longest Midwest day, about 235 miles and 8 to 9 hours. Springfield, Missouri, calls itself the birthplace of Route 66, since the number was proposed there in a telegram on April 30, 1926. Kansas has just 13 miles of the road and you drive all of them: Cars on the Route in Galena, Nelson's Old Riverton Store, the 1923 Rainbow Bridge, and the visitor center in a 1930 Phillips 66 station at Baxter Springs. In Oklahoma, a stretch of the nine-foot Ribbon Road near Miami, then the Blue Whale of Catoosa before Tulsa.

A morning on Tulsa's 11th Street, past our own office: the Meadow Gold sign, Cyrus Avery Centennial Plaza for the Tulsa man who pushed for Route 66 in the 1920s, and Buck Atom, a fiberglass spaceman. Lunch at the Rock Cafe in Stroud, built of local sandstone and open since 1939. Then the 1898 Round Barn in Arcadia and POPS, with its 66-foot neon soda bottle. Late afternoon at the Oklahoma Route 66 Museum in Clinton, then on to Elk City. About 230 miles.

The National Route 66 and Transportation Museum in Elk City opens the day. Into Texas past the empty storefronts of Texola to Shamrock, where the 1936 U-Drop Inn, an Art Deco Conoco station and cafe, now holds the town's visitor center. McLean has the Devil's Rope Museum, all barbed wire and ranch history, and the first Phillips 66 station built in Texas. In Groom the Britten water tower leans on purpose. At sunset, ten Cadillacs buried nose first west of Amarillo; spray paint is allowed. About 150 miles.

An easy 115 miles. Adrian sits at the midpoint of Route 66, 1,139 miles from Chicago and from Santa Monica, and lunch is at the MidPoint Cafe, which is known for its pies. Across the state line, Glenrio is a ghost town split between Texas and New Mexico, its motel and station shells crumbling beside the old road. You reach Tucumcari by midafternoon, with time to walk the murals and watch the neon come on along Route 66 Boulevard. Tonight is the Blue Swallow Motel, open since 1939.

In Santa Rosa, the Blue Hole is a spring-fed pool about 80 feet deep and clear enough to watch divers at the bottom, and the Route 66 Auto Museum fills a garage with hot rods and restored cars. From there you follow the 1926 to 1937 alignment north to Santa Fe for lunch near the Plaza and an hour at the Palace of the Governors, begun in 1610. Down to Albuquerque by early evening, about 240 miles in all, then a slow drive along Central Avenue as the motel signs light up.

The longest Southwest day, about 270 miles and 9 hours. West over the 1933 Rio Puerco bridge and past Laguna Pueblo to Gallup for lunch at the El Rancho Hotel, where film crews stayed in the 1940s and signed photos line the balcony. Into Arizona and Petrified Forest National Park, the only national park crossed by Route 66: the Painted Desert Inn, a 1932 Studebaker rusting beside the old alignment, and the quartz logs of Crystal Forest. A photo stop at the Wigwam Motel in Holbrook, then La Posada in Winslow.

After breakfast, Standin' on the Corner Park in Winslow, then Meteor Crater, nearly a mile across and about 550 feet deep. Through Flagstaff and 80 miles north through ponderosa pine to the South Rim of the Grand Canyon, with about four hours there. Ray walks the Rim Trail from Mather Point toward Yavapai Point, about 2 miles and nearly flat, and the free park shuttle covers Hermit Road for anyone who prefers to ride. Down to Williams for the night, the last Route 66 town bypassed by I-40, in 1984. About 210 miles.

West from Ash Fork onto the longest unbroken piece of Route 66 left, which begins at Seligman. Angel Delgadillo's barbershop is where the Historic Route 66 Association of Arizona started in 1987, and the Snow Cap Drive-In, opened by his brother Juan in 1953, still plays jokes on customers. Lunch in Seligman, then long open grassland past Peach Springs on the Hualapai reservation to the Hackberry General Store and its old cars. In Kingman, the Arizona Route 66 Museum fills the 1907 Powerhouse. About 130 miles.

The hardest stretch of road on the trip, and the most dramatic. From Cool Springs the old road climbs in tight hairpins to Sitgreaves Pass at about 3,550 feet, then drops into Oatman, where burros descended from miners' pack animals wander the main street. Cross the Colorado River at Topock into California. After Needles, the National Trails Highway runs through empty desert to Amboy and Roy's Motel and Cafe, under its 1959 boomerang sign. Coffee at the Bagdad Cafe in Newberry Springs, then Barstow. About 210 miles, 8 hours.

The last 140 miles. Elmer's Bottle Tree Ranch at Oro Grande is a field of welded pipe trees hung with glass bottles. Down through Cajon Pass to San Bernardino and the 1949 Wigwam Motel, then west along Foothill Boulevard through Rancho Cucamonga and Pasadena. Los Angeles traffic slows the final miles on Santa Monica Boulevard, so expect most of the afternoon. At the Santa Monica Pier, the End of the Trail sign marks where the road meets the ocean. Farewell dinner near the beach, with Ray's last stories of the road.

Breakfast, then a last walk on the beach path or a rented bike ride three miles south to Venice. LAX is about 10 miles from the hotel, 30 to 60 minutes depending on traffic, and a group transfer leaves at 10 am. If your flight is in the evening, the hotel holds luggage. We can also add nights in Santa Monica, or a few days in Palm Springs or San Diego, if you want to rest a little before flying home.