Routes / Iconic

Route 66: Chicago to Santa Monica

The original cross-country road trip — 3,900 km of diners, neon motel signs, and small towns that grew up around the highway itself, from Lake Michigan to the Santa Monica Pier.

3,457 km total 38h 8m driving 7 stops
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Route 66: Chicago to Santa Monica map preview
  1. 1

    Chicago

    The eastern terminus — the official Route 66 start sign sits on Adams Street downtown.

  2. 2

    St. Louis

    The Gateway Arch and a handful of surviving neon-lit Route 66 motor courts along the old alignment.

  3. 3

    Tulsa

    The Center of the Universe and the restored Blue Whale of Catoosa just outside town.

  4. 4

    Amarillo

    Cadillac Ranch — ten half-buried cars in a wheat field, covered in decades of spray paint.

  5. 5

    Albuquerque

    Central Avenue still runs straight through the old alignment, lined with Route 66-era signage.

  6. 6

    Flagstaff

    A high-altitude pine-forest town and the jumping-off point for the Grand Canyon detour.

  7. 7

    Santa Monica

    The "End of the Trail" sign on the pier — the Pacific, 3,900 km after Chicago.

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