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High Life Journeys
Route 66: Chicago to Santa Monica

Domestic USA

Route 66: Chicago to Santa Monica

The Mother Road, 2,400 miles of American myth.

ItinerariesRoute 66: Chicago to Santa Monica

The classic self-drive across eight states, from Chicago to the Santa Monica Pier.

Not every great journey is by sea. Route 66 is the original American road trip, 2,400 miles and eight states of neon motels, diners, ghost towns and big desert skies, from the shore of Lake Michigan to the Pacific. We plan it the way we plan a voyage: the right stops, the right nights, the detours worth taking (the Grand Canyon, Santa Fe), and the classic roadside stays booked ahead. You simply drive.

What you’ll do

·Cadillac Ranch, Amarillo
·Grand Canyon detour
·Historic Santa Fe plaza
·Santa Monica Pier finish
Travel style
Self-drive road trip
Typical length
10–14 days
Best season
April – October
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The route

7 stops, one seamless plan

  1. 01

    Chicago, Illinois

    Mile zero on Adams Street, deep-dish and the lakefront.

  2. 02

    St. Louis, Missouri

    The Gateway Arch and the Mississippi crossing.

  3. 03

    Tulsa & Oklahoma City

    Art-deco Tulsa and the wide open Southern Plains.

  4. 04

    Amarillo, Texas

    Cadillac Ranch, steakhouses and the Texas Panhandle.

  5. 05

    Santa Fe & Albuquerque

    Adobe plazas, green chile and high-desert light.

  6. 06

    Flagstaff & the Grand Canyon

    Ponderosa pines and a detour to the great canyon rim.

  7. 07

    Santa Monica, California

    The end-of-the-trail sign on the Pacific pier.

Why it’s special

The Mother Road

Neon motels, chrome diners and preserved stretches of the original alignment.

Big Western landscape

The Painted Desert, the Texas Panhandle and a detour to the Grand Canyon.

Planned, not winged

Right stops, right nights, classic roadside stays booked ahead, you just drive.

Begin

Let’s plan your Route 66 journey.

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