Route 66 — America's Mother Road 🛣️
2,448 miles of pure Americana: neon motor courts, painted deserts, and small-town diners running from the shores of Lake Michigan to the Pacific at Santa Monica Pier. 2026 marks the road's 100th anniversary — a perfect year to drive it. Hand-picked stays along the route and a must-see roadside icon — every link takes you straight to Trip.com to check live prices and book.
🏨 Where to Stay Along the Route
- Palmer House, a Hilton Hotel — Chicago, starting point — the longest continuously operating hotel in North America, open since 1871 just two blocks from Route 66's official "Begin" sign. French Baroque ballrooms, Tiffany chandeliers, and a guest list running from Ulysses S. Grant onward — the grandest possible send-off.
- The Skirvin Hilton Oklahoma City — historic midpoint — a beautifully restored 1911 downtown landmark currently running a dedicated "Centennial on 66" package, with James Beard-winning dining at Perle Mesta and live music at the Red Piano Lounge.
- El Rey Court — Santa Fe, boutique hidden gem — a 1936 adobe motor court reimagined with a retro-chic Southwest look, set across five acres of old-growth gardens with a heated pool and mezcal cocktails at La Reina — genuinely one of the most atmospheric stops on the whole route.
- La Posada Hotel and Gardens — Winslow, Arizona — the last of the grand Fred Harvey trackside hotels, designed in 1930 by architect Mary Colter, with lush gardens, an on-site art gallery, and the celebrated Turquoise Room restaurant. The only US hotel with its own Amtrak stop at the door.
- Fairmont Miramar Hotel & Bungalows — Santa Monica, journey's end — a historic 1875 estate turned resort atop the Santa Monica bluffs, with private garden bungalows, five restaurants and bars, and past guests from Greta Garbo to Marilyn Monroe. A fitting, palm-lined finale a short walk from the "End of the Trail" sign at Santa Monica Pier.
✈️ Flights
🎟️ Experiences
- Cadillac Ranch — ten vintage Cadillacs buried nose-first in a Texas Panhandle field outside Amarillo, angled to match the Great Pyramid of Giza and covered in ever-changing layers of visitor graffiti. Bring a can of spray paint and leave your mark on one of Route 66's most famous, most photographed stops.
🚗 Car Hire & Transfers
- Car Hire — Chicago O'Hare or Midway — essential for this trip; a one-way rental picked up in Chicago and dropped off in Los Angeles is the standard way to drive the Mother Road. Budget 10-16 days to do it justice, with the stretch from New Mexico through Arizona considered the most scenic and best-preserved.
- Airport Transfers — useful for the Chicago and Los Angeles legs of the trip, before and after the drive itself.