Roys motel cafe amboy route 66 neon sign sunset
Home / Journeys / Epic Route 66 Road Trip – From Chicago to Los Angeles
22 nights · Chicago · Car

Epic Route 66 Road Trip - From Chicago to Los Angeles

Sleep in a motel that hasn’t changed its sign since the 1960s, in a town outlaws once used to disappear, on a road that’s been slowly disappearing itself for decades – twenty-two nights the entire length of Route 66.

From$6,874pp
Duration22 days
StyleSelf-guided
Find out more
An independent Stradora pick. Details from the operator's published information, last checked 31 Oct 2026. Stradora DiscoveryChosen independently by our editors because we think it's worth the drive. We're not partnered with this operator: dates, prices and booking are handled by them, and we last checked their published details on 31 Oct 2026.
Booked with the operator?

Tell us your trip details and we'll put together a complimentary Stradora Expedition Pack for the journey.

Claim your pack

The route

Twenty-three days on Route 66 from Chicago to Los Angeles, 2,250 miles across eight states, which is the full version rather than a sampler.

Chicago opens it with three nights and live jazz at Andy’s, then Springfield in Illinois, then St Louis and the Gateway Arch, which at 192 metres is the tallest arch in the world and is ridden to the top in small pods. Springfield in Missouri follows via the Meramec Caverns, which the James brothers reportedly used as a hideout, and the Ozarks.

Tulsa comes next for its Art Deco district, built on oil money in the 1920s, then Oklahoma City and the National Cowboy Museum. Amarillo follows with the Big Texan Steak Ranch, a Route 66 institution moved to its present site when the interstate bypassed the old road, then Tucumcari and a 1960s motel of the kind the route is remembered for.

Santa Fe gets two nights of adobe architecture and the Museum of Indian Arts and Culture below the Sangre de Cristo mountains. Gallup follows via the ghost towns of Los Cerrillos and Madrid, then Holbrook with Canyon de Chelly and its Ancestral Puebloan cliff dwellings, and the route continues through Arizona to the Grand Canyon and on to Los Angeles. Original Travel include the hire car, accommodation, the passes and tours, concierge access, a 24-hour helpline and carbon absorption. International flights and most meals are separate. Prices run from 5,150 to 7,200 pounds per person, which for twenty-three nights with a car is reasonable value.

Style
Self-guided
Duration
Grand tour (16+ nights)
Region
North America
Vehicle provision
Vehicle provided
Departures
Flexible, tailor-made
Starts/ends
Chicago, United States to Los Angeles, United States
Run by
Independent specialist operator

What's included

  • Hire car
  • accommodation
  • Chicago Explorer Pass
  • dinner and a jazz show (Andy's Jazz Club)
  • Grand Canyon viewing platform access
  • Wi-Fi router and e-SIM
  • local Concierge access
  • 24-hour helpline
  • carbon absorption on the trip's footprint (operator's own programme).

Not included

  • International flights
  • meals beyond those specified
  • not itemised in full.

Ready to drive it?

22 days, from $6,874pp

Independent Stradora pick
Find out more
0 journeys selected Compare Now