13 days / 12 nightsTour starts ChicagoTour ends New Orleans
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Overview
Follow the soulful rhythms of America on this self-drive journey through the heartland. Start in Chicago's blues clubs, cruise historic Route 66, and soak in Memphis's rock 'n' roll legacy. Experience Nashville's country vibes before ending in vibrant New Orleans, where jazz fills the French Quarter. With handpicked accommodations including the iconic Nobu Hotel Chicago and Four Seasons St. Louis, this flexible road trip lets you set your own pace while exploring music's most legendary destinations.
Itinerary
What you’ll do each day, with your included hotel — or upgrade any stay.
Arrive in the Windy City, where the musical journey begins. Spend your first days exploring Chicago's legendary blues clubs, visiting the iconic Route 66 starting point, and enjoying world-class dining and architecture. Take in a live blues show in historic neighborhoods like South Side or Lincoln Park.
Make this trip yours
Stay longer or shorter in Chicago
Your stay in Chicago
3 nights13 days total
Your itinerary and price update when you change your stay.
Days 1–4 Included
Travelodge by Wyndham Downtown Chicago
Chicago
Recommended nights Fully flexible
Adjust the number of nights at this hotel — your itinerary days and price update automatically.
More Hotel Options
Included
Travelodge by Wyndham Downtown Chicago
Selected
Le Meridien Essex Chicago
Warwick Allerton Chicago
Holiday Inn & Suites Chicago - Downtown by IHG
Freehand Chicago
Club Quarters Hotel, Central Loop, Chicago
The Allegro Royal Sonesta Hotel Chicago Loop
Congress Plaza Hotel
Staypineapple, An Iconic Hotel, The Loop
Nobu Hotel Chicago
Rental car
Chicago O'Hare, IL 13 days
Chevrolet Trax
Included
Compact SUV · Hertz
Automatic 5 A/C Unlimited miliage
What's Included
Your chosen vehicle upon arrival,with unlimited mileage and basic insurance (additional coverage available if selected).
Confirmed and prepaid Hotel reservations at the properties you've selected.
Digital itinerary guide with daily routes, tips, and local insights
What's Excluded
International flights to/from the starting point
Hotel taxes and resort fees (payable locally, cannot be prepaid)
Days 1–4 Included
Europe
Americas
Africa