Music City to Windy City

Tour Duration 13 Nights - From $4299*

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Join an escorted music tour from Music City to Windy City!

If you want unforgettable memories and great value for money, join us on this musical journey from Nashville Tennessee to Chicago Illinois on our Music City to Windy City escorted tour. Enjoy the music and attractions that each area has to offer. It’s an informal, friendly and fun trip designed with music lovers in mind! You will discover all the different types of music and meet local people who will tell you the stories of its origins. Travelling Time has unique and exclusive access to people and places other companies simply cannot reach.

Music City to Windy city Music Bar
Nashville Daytime
Louisville Downtown
Cleveland Skyline
Chicago Daytime


Welcome to our Music City to Windy City Tour! Once you are checked in to your Nashville Hotel - feel free to join your guide and driver for a welcome meeting and to get to know your fellow travellers.

Discover why Nashville, the capital of Tennessee, is called Music City USA! As you explore the downtown area you’ll find many famous attractions including The Country Music Hall of Fame and The Historic Ryman Auditorium, The Johnny Cash & Patsy Cline Museums celebrate the lives of these famous stars of Country Music. On Broadway and in Printers Alley you’ll hear some of the best live music in the world famous honky-tonks. Then of course great music venues like the Opry House, home of the famous “Grand Ole Opry” stage and RCA’s Studio B are within easy reach.

More free time to enjoy the wonderful music and attractions that can be found in and around Nashville. How about a trip out to the Opryland Area and take a leisurely cruise on the General Jackson Showboat, "sail" around the Opryland Hotel and perhaps pop into a couple of the area’s famous honkytonks. Nashville Palace and John A's Roadhouse are nearby for great food and live music. There is also shopping and several restaurants at Opry Mills and Madame Tussaud's can be found here too!

On your last day in Nashville - be sure to visit the wonderful Centennial and Bi-Centennial Parks and a visit to the Parthenon is a must. Make sure you buy your cowboy boots on Lower Broadway and kick your heels on Printers Alley tonight - before getting ready to continue our travels tomorrow.

As we wave goodbye to Nashville we will travel North into Kentucky, the Bluegrass State. Our first stop will be the picturesque small town of Franklin with its lovely courtyard square. Learn why Country Legends Johnny Cash & June Carter tied the knot here and visit the Mennonite Community for lunch! This afternoon we will travel the short distance to Bowling Green to tour the fabulous Corvette Museum. Then it's back to Franklin for dinner and music at the Brickyard Cafe!

Travelling North through Kentucky we reach Central City, home to the wonderful Everly Brothers Museum...after our tour and lunch we will continue on to Louisville. Kentucky's largest city sits on the Ohio River along the Indiana border. We will spend the evening downtown enjoying dinner and local entertainment.

This morning we will take you to The Muhammad Ali Center which is dedicated to the boxer Muhammad Ali, a native of Louisville. You will then have free time to explore some of the museums and landmarks that make Louisville famous. Did you know that, every May, its race course Churchill Downs hosts the Kentucky Derby whose long history is explored at the Kentucky Derby Museum. Baseball is celebrated at the Louisville Slugger Museum and Factory, where Major League bats are produced and a giant baseball "slugger" marks the entrance.

Today we leave Kentucky and head into Ohio and our first stop is Cincinnati, where we will have lunch in the Over-the-Rhine district that is known for its 19th century architecture. Then it is on to Cleveland. This vibrant city is home to arts, culture, and landmarks that pay homage to the history of music. Made up of "Districts" like Cleveland Heights, Little Italy, Shaker Square, Downtown and filled with world-class theatre, live music and noteworthy nightlife there is so much to see and do in Cleveland!

One of Cleveland’s top attractions is The Rock & Roll Hall of Fame and Museum. After our visit to this iconic building, join us on a guided tour of the City’s districts followed by free time to explore this fascinating city at your own pace.

As we make our way to Detroit today we will stop in the city of Toledo Ohio, situated on the western tip of Lake Erie. We will visit the city's Glass Pavilion which showcases thousands of glass works, before stopping for lunch and pie! We will travel around Lake Erie to Detroit - the largest city in the state of Michigan. The city’s ties to the auto industry, gave it the nickname "Motor City.

This morning we will visit “Hitsville U.S.A” home to Motown Records. After our tour of this wonderful museum, it’s off to Kalamazoo for lunch and a visit to a local brewery. Then we’ll travel rest of the way to Chicago!

A local guide will escort us on a city tour today and you will have the opportunity to hop on and off the bus at places of interest throughout the city. This evening we will take you to a few more of the city’s fantastic blues clubs!

On our final day in the Windy City, we’ll spend time at Navy Pier then onto Lake Michigan for a City Skyline Tour. Afterwards, we will spend our last evening in Chicago enjoying a meal and a few drinks together while we listen to some local music!

Today our Music City to WIndy City tour ends and it’s time to travel to the airport for your journey home.


Book Now Clock


Our Music City to Windy City Escorted Group Tours are scheduled to depart:
9th June 2025
If these dates are not suitable, please call us on 01738 643737 to discuss our small group option.


Book The Bus


At Travelling Time we offer exceptional value for money on our fixed price escorted tours. We include transportation to suit your group size, hotel accommodation, meals as described and all attractions listed in our itineraries.


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Tour prices are shown without flights. You are free to make your own arrangements or purchase a flight inclusive tour with us. Available from all major UK Airports, flight inclusive tours are ATOL protected so you can book with complete confidence.