America's most storied highway, rolling from Chicago through the heartland and Southwest to the California coast, past neon motels, ghost towns and the Grand Canyon detour.
Duration: 14 days Best time: May–June & September–October (comfortable temperatures across the Plains and desert) Region: Midwest
A big one-way drive of ~2,400 miles / 3,900 km. Fly into Chicago, out of Los Angeles.
Day by day
- Day 1–2Chicago, Illinois
Start at the 'Route 66 Begin' sign on Adams Street; deep-dish, the lakefront and the Art Institute before you roll.
- Day 3Illinois → St. Louis, Missouri
Classic Illinois 66 towns and the Chain of Rocks Bridge into St. Louis for the Gateway Arch.
- Day 4–5Missouri → Tulsa & Oklahoma City
Meramec Caverns, then Oklahoma's long, well-preserved stretches and Art Deco Tulsa.
- Day 6Oklahoma → Amarillo, Texas
The Texas Panhandle and the spray-painted Cadillac Ranch; a Big Texan steak if you dare.
- Day 7Texas → Tucumcari & Santa Fe, New Mexico
Neon-lit Tucumcari motels, then a detour up to adobe Santa Fe.
- Day 8Albuquerque
Old Town and Central Avenue neon; the classic New Mexico 66 alignment.
- Day 9New Mexico → Flagstaff, Arizona
The Petrified Forest and Painted Desert, then pine-clad Flagstaff.
- Day 10Grand Canyon detour
Head north for a day at Grand Canyon National Park's South Rim — the trip's natural climax.
- Day 11Seligman & Oatman, Arizona
The kitschy heart of old 66 — Seligman's memorabilia and Oatman's wild burros.
- Day 12–13Mojave → Los Angeles
Cross the Mojave via Barstow to the LA basin and the coast.
- Day 14Santa Monica Pier
The 'End of the Trail' sign on the pier — 66 finishes at the Pacific.
