Route 66 — Chicago to Santa Monica
The Mother Road — 3,940 km, 8 states, one bucket-list drive
The original Route 66 was decommissioned in 1985, but the 'Historic 66' brown signs still guide you across 8 states. Do it east-to-west (Chicago → Santa Monica) to end at the Pacific. Two weeks is a sprint, three is human. Don't try to stay on the old road 100% — mix Interstate 40 where 66 disappears.
Day-by-day route
Lou Mitchell's diner + Route 66 begin sign + Gateway Arch
Meramec Caverns + Blue Whale of Catoosa
Cadillac Ranch + Big Texan 72oz steak
Tucumcari neon motels + Petroglyph National Monument
Petrified Forest + Meteor Crater + Wigwam Motel
Grand Canyon side trip + Seligman (Radiator Springs inspiration)
Oatman burros + Barstow + Santa Monica Pier end sign
Grand Canyon lodging 6 months out, iconic motels (Wigwam, Blue Swallow) 3 months out, one-way rental with unlimited miles.
Long empty stretches in Texas/NM — fill up every chance. Summer 40°C+. Never sleep in a car in some smaller towns.
Other road trips worth planning
Discover Cars, Aviasales, Airalo and EKTA links are affiliate — we may earn a small commission at no extra cost to you. Distances and prices reviewed for 2026.