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Classic Route 66 Road Trip: Chicago to Santa Monica

A 10-day itinerary covering 20 stops. Route: Lou Mitchell's → Route 66 Hall of Fame and Museum → Meramec Caverns → Cars on the Route → Oklahoma Route 66 Museum → Midpoint Cafe → 66 Diner → Petrified Forest National Park → Oatman Ghost Town → Wigwam Motel #7 → Santa Monica Pier.

10days
20stops
1825km
DAY01

Lou Mitchell's → Gemini Giant

95 km · 1h 3m driving · Overnight in Gemini Giant
  1. 09:00
    Lou Mitchell's· start
  2. 95 km · 1h 3m
  3. 12:00
    Gemini Giant· overnightMust-see
DAY02

Route 66 Hall of Fame and Mus… → Cozy Dog Drive-In

70 km · 44m driving · Overnight in Cozy Dog Drive-In
  1. 09:00
    Route 66 Hall of Fame and Museum· startMust-see
  2. 70 km · 44m
  3. 12:00
    Cozy Dog Drive-In· overnight
DAY03

Meramec Caverns → 66 Drive-In Theatre

255 km · 2h 26m driving · long drive · Overnight in 66 Drive-In Theatre
  1. 09:00
    Meramec Caverns· startMust-see
  2. 255 km · 2h 26m
  3. 12:00
    66 Drive-In Theatre· overnight
DAY04

Cars on the Route → Blue Whale of Catoosa

32 km · 28m driving · Overnight in Blue Whale of Catoosa
  1. 09:00
    Cars on the Route· start
  2. 32 km · 28m
  3. 12:00
    Blue Whale of Catoosa· overnightMust-see
DAY05

Oklahoma Route 66 Museum → Cadillac Ranch

334 km · 3h 2m driving · long drive · Overnight in Cadillac Ranch
  1. 09:00
    Oklahoma Route 66 Museum· start
  2. 334 km · 3h 2m
  3. 12:00
    Cadillac Ranch· overnightMust-see
DAY06

Midpoint Cafe → Blue Swallow Motel

64 km · 36m driving · Overnight in Blue Swallow Motel
  1. 09:00
    Midpoint Cafe· start
  2. 64 km · 36m
  3. 12:00
    Blue Swallow Motel· overnightMust-see
DAY07

66 Diner → El Rancho Hotel

282 km · 2h 38m driving · Overnight in El Rancho Hotel
  1. 09:00
    66 Diner· startMust-see
  2. 282 km · 2h 38m
  3. 12:00
    El Rancho Hotel· overnight
DAY08

Petrified Forest National Park → Wigwam Motel

185 km · 1h 43m driving · Overnight in Wigwam Motel
  1. 09:00
    Petrified Forest National Park· startMust-see
  2. 185 km · 1h 43m
  3. 12:00
    Wigwam Motel· overnight
DAY09

Oatman → Elmer's Bottle Tree Ranch

425 km · 4h 10m driving · long drive · Overnight in Elmer's Bottle Tree Ranch
  1. 09:00
    Oatman Ghost Town· startMust-see
  2. 425 km · 4h 10m
  3. 12:00
    Elmer's Bottle Tree Ranch· overnight
DAY10

Wigwam Motel #7 → Santa Monica

83 km · 55m driving
  1. 09:00
    Wigwam Motel #7· start
  2. 83 km · 55m
  3. 12:00
    Santa Monica PierMust-see
Heads Up
  • Day 3: 5h 47m driving — plan rest stops
  • Day 5: 5h 41m driving — plan rest stops
  • Day 9: 7h 23m driving — plan rest stops