Route 66: Chicago to Santa Monica

Overview

America's Main Street still runs 2,400 miles from a brown sign on Adams Street in Chicago to the pier at Santa Monica, and driving it end to end remains the definitive American road trip. The interstate long ago bypassed the Mother Road, which is exactly the point: you trade speed for neon motels in Tucumcari, the half-buried Cadillacs of Cadillac Ranch outside Amarillo, and the burros that mob your car in Oatman, Arizona. The moment that stays with you comes west of Seligman, where the longest unbroken stretch of original 66 rolls through empty high desert with the railway for company, and you finally understand the fuss. The variable that catches people out is pacing: two weeks is the honest minimum, and squeezing it into ten days turns the trip into interstate slog. Navigation is the other trap — old alignments go unsigned, so carry the EZ66 guide alongside the sat-nav. Fly into Chicago, drop the hire car in Los Angeles (one-way fees sting), and budget around £2,200 per person for fourteen nights of motor courts, fuel, diners and pie.

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Prefilled for 1 October 2026 — the next best-season window. Search on partner sites — opens in a new tab.