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Wind down those windows, tune the radio and enjoy the open road as you make your way through the USA’s legendary highway

Route 66 is a bucket-list favourite and in a land of self-drives our itineraries are the best way to enjoy Chicago and Route 66’s legendary highlights. Start your epic cross-country journey in the ‘Windy City’, but not before you’ve made time to learn about some of its striking buildings on a Chicago Architectural River Cruise or teetered on the glass ledge that extends from the Skydeck on the 103rd floor of Willis Tower (the tallest building in the Western Hemisphere). Affectionately dubbed 'The Mother Road', you can enjoy this classic highway as you tour through Missouri, Oklahoma, Texas, New Mexico, Arizona and Nevada, finally stopping in Los Angeles as you complete your 2,400+ mile trip. Destinations, durations and accommodation are all completely flexible and easily adapted to suit your own needs.

Our recommened Chicago and Route 66 tours

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Historic Route 66 self-drive

Step back in time to the golden age of road travel on one of the world’s famous highways, Route 66. Your epic 2000-mile journey will be full of kitsch and quirky Americana.

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