📍 United States

MOTHER ROAD SOUTH: CHICAGO BLUES TO CRESCENT CITY JAZZ

Electric blues crackling through night air, clubs pulsing with Delta rhythms, second-line umbrellas twirling in parade. Route 66 heading south.

≈ 17
Days
2068
Km
7
Stops
📖 9 min read 🔄 Last updated: 2026-01-17

Connect Chicago to New Orleans following music roads, with a detour through St. Louis and its riverbanks. Make Nashville pulse in concert halls, then dive into Memphis between studios and blues. Then cross the Mississippi Delta, dark bars and electric guitars, before reaching New Orleans and its second-line parades. An itinerary where each stage has its soundtrack.

Your day-by-day itinerary

1
Day

Chicago

electric blues chess records magnificent mile

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5 photos
Day 1
🔍

Discover

1
Millennium Park and Cloud Gate
2
Art Institute of Chicago (major collections)
3
Architectural walk on Michigan Avenue and the Loop
🎯

Activities

→
Riverwalk at sunset
2
Day

Chicago

electric blues chess records magnificent mile

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5 photos
Day 2
🔍

Discover

1
Navy Pier and lakefront
2
Museum Campus — exterior views Field Museum & Shedd Aquarium
3
360 Chicago (John Hancock Center) — panorama
🎯

Activities

→
Walk on the Old Chain of Rocks Bridge (historic portion of Route 66)
🚗
Next stop
Distance: 480 km
Travel time: 4h45
3
Day

St Louis

arch city route sixty-six riverboat jazz

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7 photos
Day 3
🔍

Discover

1
Springfield (IL) — Lincoln Tomb at Oak Ridge Cemetery
2
Arrival in St. Louis — Gateway Arch National Park (exteriors + museum)
3
Country Music Hall of Fame & Museum
🎯

Activities

→
Discovery of murals (The Gulch: "Wings" by Kelsey Montague)
🚗
Next stop
Distance: 465 km
Travel time: 4h20
4
Day

Nashville

music row bluebird cafe songwriter soul

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4 photos
Day 4
🔍

Discover

1
Ryman Auditorium — backstage tour
2
Walk on Broadway (signs and music venues)
3
Johnny Cash Museum & Café (museum)
🎯

Activities

→
Live country music session (historic venue or recorded show)
5
Day

Nashville

music row bluebird cafe songwriter soul

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4 photos
Day 5
🔍

Discover

1
Bicentennial Capitol Mall State Park & Farmers' Market (stroll)
2
Nashville Parthenon (replica, Centennial Park — exteriors and gallery)
3
Belle Meade Historic Site & Winery (historic visit, heritage focus)
🎯

Activities

→
Grand Ole Opry (concert scheduled according to availability)
6
Day

Nashville

music row bluebird cafe songwriter soul

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4 photos
Day 6
🔍

Discover

1
Musicians Hall of Fame & Museum
2
Sun Studio — guided tour
🎯

Activities

→
Mississippi Riverfront (Tom Lee Park) — sunset
🚗
Next stop
Distance: 341 km
Travel time: 3h15
7
Day

Memphis

sun records stax museum river city

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3 photos
Day 7
🔍

Discover

1
Beale Street — heritage walk (facades, musical landmarks)
2
Slave Haven Underground Railroad Museum (Burkle Estate)
3
Graceland — visit to the main exhibitions
🎯

Activities

→
Big River Crossing (pedestrian bridge over the Mississippi)
8
Day

Memphis

sun records stax museum river city

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3 photos
Day 8
🔍

Discover

1
Old Capitol Museum (state history)
2
Vicksburg National Military Park (battlefield, museum)
🎯

Activities

→
Mud Island River Park — Mississippi model & views
9
Day

Memphis

sun records stax museum river city

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3 photos
Day 9
🔍

Discover

1
Natchez National Historical Park — Melrose (house and gardens)
🎯

Activities

→
Walk around the Mississippi State Capitol (exteriors)
🚗
Next stop
Distance: 338 km
Travel time: 3h15
10
Day

Jacksonville

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3 photos
Day 10
🔍

Discover

1
Bluff Park — views of the Mississippi
2
Oak Alley Plantation — exhibitions on slavery and the site
🎯

Activities

→
Portion of the Natchez Trace Parkway — scenic route
🚗
Next stop
Distance: 164 km
Travel time: 2h
11
Day

Natchez

pilgrimage mansions natchez trace historic bluff

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10 photos
Day 11
🔍

Discover

1
Arrival in New Orleans — French Quarter (Jackson Square, St. Louis Cathedral)
2
Garden District — historic houses (self-guided walk)
3
Lafayette Cemetery No.1 (exterior visit/depending on access)
🎯

Activities

→
Walk on Royal Street & Chartres Street (Creole architecture)
🚗
Next stop
Distance: 280 km
Travel time: 3h30
12
Day

New Orleans

treme second-line garden district gumbo

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8 photos
Day 12
🔍

Discover

1
New Orleans Jazz Museum (Old U.S. Mint)
2
Treme & Louis Armstrong Park — heritage walk
🎯

Activities

→
Mississippi River cruise aboard the Steamboat Natchez (or equivalent)
13
Day

New Orleans

treme second-line garden district gumbo

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8 photos
Day 13
🔍

Discover

1
The Historic New Orleans Collection (museum & archives)
2
Faubourg Marigny & Frenchmen Street — galleries and music (daytime stroll)
3
City Park — Besthoff Sculpture Garden
🎯

Activities

→
Basketball game (Smoothie King Center) according to schedule
14
Day

New Orleans

treme second-line garden district gumbo

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8 photos
Day 14
🔍

Discover

1
Treme & Louis Armstrong Park — heritage walk
2
The Historic New Orleans Collection (museum & archives)
🎯

Activities

→
Final views of the Mississippi at the Moonwalk near Jackson Square
15
Day

New Orleans

treme second-line garden district gumbo

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8 photos
Day 15
🔍

Discover

1
Faubourg Marigny & Frenchmen Street — galleries and music (daytime stroll)
2
City Park — Besthoff Sculpture Garden
🎯

Activities

→
Final views of the Mississippi at the Moonwalk near Jackson Square

🗺️ Itinerary map

🗺️ Nearby itineraries

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🛡️ Travel advice - United States

Check official recommendations

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❓ Frequently asked questions

What weather should you expect?

Spring (April-May): Perfect weather across most regions (15-25°C) with blooming landscapes, moderate crowds, and excellent conditions for national parks and cities. Ideal for diverse activities nationwide.

Autumn (September-October): Excellent temperatures with spectacular fall foliage, harvest festivals, and comfortable weather. Perfect for outdoor activities, cultural events, fewer crowds than summer.

Summer (June-August): Peak season with warmest weather but highest crowds and prices. Excellent for northern regions, challenging in southwestern deserts, perfect for beaches and national parks.

Winter (December-February): Variable conditions from tropical Florida to snowy Colorado. Perfect for skiing, southern destinations, indoor attractions, lowest prices outside holiday periods.

How many days should I plan?

We believe you will enjoy this itinerary best by dedicating between 14 and 20 days. The next step will allow you to adjust the duration of your stay.

What to discover in United States?

Continental diversity with iconic landmarks, cultural melting pot, and endless possibilities. Experience natural wonders, vibrant cities, and authentic American dreams from coast to coast. The country offers incredible diversity with modern amenities and cultural richness. United States provides life-changing experiences with natural beauty and cultural authenticity.