Route 66 Road Trip: The Ultimate Itinerary for Chicago to Santa Monica - Time Out

The most iconic American road trip is the 2,451-mile Route 66, one of America's original highways. Recently, this road well-traveled has faced a retro renaissance with renewed popularity from travelers eager for slow travel and a classic road trip.

Established in 1926 and completed in the 1930s, Route 66 was the primary highway for folks seeking to drive to the west coast. Connecting Chicago to Santa Monica, California, Route 66 passes through eight states (Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California). 

What makes the multi-day road trip appealing are the slices of 20th century Americana and kitsch: mom-and-pop motels, retro soda fountains and service stations, neon-lit diners, and quirky roadside attractions. Follow our ultimate road trip itinerary so you won't miss any of the nostalgic fun.

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