Historic Route 66

Sixteen nights from Chicago to Santa Monica, self-guided, 2,400 miles along the full length of Route 66 across eight states.

The whole road, end to end, with the flights and the one-way car hire in the price, and the operator is honest about the one real difficulty: satellite navigation will route you round the original alignments rather than along them, so the road book matters.

Chicago opens it, then Springfield in Illinois by way of Joliet, the Gemini Giant at Wilmington and the Route 66 Hall of Fame at Pontiac. St Louis follows for two nights with the Gateway Arch, then Springfield in Missouri, Tulsa by way of the Ribbon Road, the oldest and narrowest surviving stretch, and Oklahoma City with Pops Soda Ranch and its six hundred varieties. Amarillo comes next with the Cadillac Ranch, then Santa Fe by way of the Midpoint Cafe, the halfway mark, and the ghost town of Glenrio. Albuquerque, Gallup and two nights at Flagstaff follow, with the Petrified Forest, Meteor Crater, the corner at Winslow and the Grand Canyon optional, then Barstow by way of Seligman, and the pier at Santa Monica.

The flights out to Chicago and home from Los Angeles, the car hire with GPS and fifteen nights’ accommodation plus one on the flight are included, with meals depending on the room basis; national park fees are extra and the pass arrangements for non-US residents changed in 2026, so they are worth checking. The price shown is per person. Spring and autumn are the seasons.