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Route 66: Chicago to Santa Monica

Itinerary through Chicago, St. Louis, Tulsa, Amarillo, Santa Fe, Flagstaff, … (13 days), with day-by-day ideas, shared by a Voyageur traveler.

United States · 13 days · 8 Stages

Chicago, United States

Days 1–3

  • Day 1 16:00: Photo at the “Begin Route 66” sign
  • Day 2 10:00: Architecture river cruise
  • Day 2 13:00: Art Institute of Chicago
  • Day 2 19:00: Deep-dish pizza at Lou Malnati’s

St. Louis, United States

Days 3–4

  • Day 3 18:00: Gateway Arch tram to the top
  • Day 3 20:30: Frozen custard at Ted Drewes

Tulsa, United States

Days 4–5

  • Day 4 19:00: Cain’s Ballroom and the Tulsa Arts District

Amarillo, United States

Days 5–6

  • Day 5 19:00: Big Texan Steak Ranch — the 72 oz challenge (optional)

Santa Fe, United States

Days 6–8

  • Day 6 17:00: Plaza and Palace of the Governors
  • Day 7 10:00: Meow Wolf House of Eternal Return
  • Day 7 15:00: Canyon Road galleries
  • Day 7 19:30: Green chile at The Shed

Flagstaff, United States

Days 8–10

  • Day 9 06:30: Grand Canyon South Rim sunrise at Mather Point
  • Day 9 10:00: Rim Trail to Hopi Point
  • Day 9 21:00: Lowell Observatory night sky

Barstow, United States

Days 10–11

  • Day 10 17:00: Bottle Tree Ranch

Santa Monica, United States

Days 11–13

  • Day 11 18:00: “End of the Trail” sign on Santa Monica Pier
  • Day 12 10:00: Bike ride to Venice Beach
  • Day 12 15:00: Griffith Observatory