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Hit the open road from the ‘Windy City’

Take an unforgettable trip from one of USA’s biggest and best cities. Chicago is home to incredible jazz and blues, fantastic arts and culture, towering architecture and delicious deep dish pizza.

Many of USA’s best self drive itineraries begin in the Windy City – but the most famous is the iconic Route 66 – drive a total of 2,448 miles across eight states from the prairies of the mid-west and Texas to the deserts of New Mexico and Arizona, including Las Vegas and the breath taking Grand Canyon, before finally taking you through Los Angeles and the finishing point on Santa Monica Pier.

Use Chicago as your starting point before heading out on the open road – discover Kentucky’s fantastic bourbon trail, head to the Deep South for a musical pilgrimage in ‘Music City’ Nashville and the land of the Delta Blues – Memphis. Why not explore the picturesque Great Lakes region or follow the mighty Mississippi River to Mardi Gras city – New Orleans to soak up the laid back atmosphere and Creole cuisine.

Self drive holidays allow you the freedom and flexibility to really explore at your own pace and to take control of your own epic adventure – whether you decide to travel by car, motorhome or even motorbike.

Or try these inspiring itineraries


Here’s a selection of popular itinerary suggestions to give you an idea of what’s available. Call us now and we’ll create an amazing holiday just for you.

Route 66

Route 66 Road Trip Holiday

  • 16 Days
  • Guide Price £2,399 PP
Our Historic Route 66 Self Drive is a journey you’ll never forget, beginning in Chicago and ending at the Santa…
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Family holidays
a large body of water with a city in the background

Great American Road Trip

  • 22 Days
The Great American Roadtrip Self Drive is an epic 5,000km journey from New York City to San Francisco, taking in…
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Self drive holidays
Eaglerider road trip along Route 66

Route 66 Guided Motorcycle Tour

  • 15 Days
  • Guide Price £5,299 PP
The EagleRider Route 66 Guided Motorcycle Tour is a journey to the American interior on the world’s most famous road…
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Iconic journeys

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