roadbook.us· @roadbook.us· Posted Apr 2026

Historic Route 66: Chicago to Santa Monica

A 20-stop road trip: Chicago → Santa Monica. Planned with Roadbook.

  • 20 stops
  • ~1,942 mi
  • ~1d 15h drive
  • 22 nights
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The route

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The itinerary

20 stops on this route.

  1. 86 mi· ~1h 44m
  2. 92 mi· ~1h 51m
  3. 86 mi· ~1h 44m
  4. 258 mi· ~5h 12m (Long driving day)
  5. 7 mi· ~8 min
  6. 98 mi· ~1h 59m
  7. 82 mi· ~1h 39m
  8. 256 mi· ~5h 9m (Long driving day)
  9. 47 mi· ~57 min
  10. 60 mi· ~1h 12m
  11. 165 mi· ~3h 20m
  12. 122 mi· ~2h 27m
  13. 116 mi· ~2h 20m
  14. 55 mi· ~1h 7m
  15. 31 mi· ~37 min
  16. 39 mi· ~47 min
  17. 88 mi· ~1h 46m
  18. 150 mi· ~3h 1m
  19. 104 mi· ~2h 5m

Sources

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