Chicago Road Trip

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.