Self Drive Chicago

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.

16 days

Route 66 Holidays

Guide Price £2,349 pp

Route 66 has to be on everyone's wish list and so let us make those wishes come true. Established back in 1926, famously known as Route 66 and covering a total of 2,448 miles across eight states, this journey will...

Iconic journeys

22 days

The Great American Roadtrip

Guide Price £3,349 pp

Take a scenic tour through 12 of America's 50 states passing by iconic sights, breathtaking landscapes and tasting delicious food and drink. You'll see the best of America on this trip of a lifetime. Discover the sights of New York,...

Self drive holidays

15 days

EagleRider Route 66 Guided Motorcycle Tour

Guide Price £4,729 pp

The quintessential USA road trip but only this time cruising in style on a classic dream machine motorcycle! Take our 15 night escorted tour along the USA's Mother Road all the way from Chicago through eight states past 1950's nostalgia...

USA road trips

How we tailor make your holiday

1. Browse

Look through our website for inspiration, then call our Destination Specialists

2. Create

We'll listen to your wish-list and use our knowledge to design a unique itinerary

3. Customise

We'll keep on refining until we've created your perfect personalised holiday

Talk to our experts

01293 762404

The Hayes & Jarvis Way

We’ve been tailor making holidays for 65 years. With over 60 destinations  to choose from, talk to us and we’ll listen to your travel ideas to create  unforgettable holiday experiences.

Email sign-up

Self Drive Chicago

Hit the open road from the 'Windy City'

Chicago River Tours

Eleven Diner

Cloudgate, Millennium Park

Route 66 Beginning

Route 66

Grand Canyon National Park

Las Vegas Strip

City Views from the Hollywood Hills

Route 66

Split Rock Lighthouse

Kentucky Derby

Royal Street