Chicago Tours

Inspiration for your own tailor-made trip

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The Musical Highway - From Chicago and Nashville to New Orleans and Austin

Pump up the volume on this tuneful two-week adventure along America’s musical highway, cruising through Chicago, Nashville, New Orleans and Austin

15 days, from £3100 to £5000

Jazz, Rhythm and Blues - USA's Deep South by Train

Feel the rhythm of the Deep South on this 15-day train journey through its jazz, blues and country hotspots

15 days, from £3100 to £4550

Discover The USA's Great Lakes - Shoreline Towns and Soulful Cities

Explore the USA’s Great Lakes over 14 days, including two of the most beautiful: Lake Michigan and Lake Superior

19 days, from £3450 to £5500

Hops, Highways & Honky-tonks - A Craft Beer Road Trip Across the Midwest

Hit the road for 18 days of pints and pitstops in quirky towns from Chicago to Nashville

18 days, from £3600 to £5150

Secrets of the Midwest - Chicago and the Great Lakes

Uncover the marvels of the Midwest on this 15-day exploration through one of America’s most humble regions

15 days, from £4600 to £6200

Epic Route 66 Road Trip - From Chicago to Los Angeles

Trace a century of cross-country travel on this epic 23-day road trip along the iconic passage of Route 66

23 days, from £5150 to £7200

100% tailor-made holidays

Understanding Your Needs

Our team of destination experts will get to know you and your unique requirements for your holiday

Personalisation

We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities

Our Services

All of our holidays include little extras designed to make a big difference to your trip, from checking you in for your flights to our network of local Concierges