Route 66 Itinerary – 14 Days from Chicago to Santa Monica

by CommonRoads | Jul 17, 2025 | Long Road Trips

From the moment you pause beneath the iconic “Begin Route 66” sign in downtown Chicago, you’re not just embarking on a two-week-long drive; you’re stepping into a living legend. Spanning 2,448 miles across eight states, the Mother Road, officially born in 1926 and...

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