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Music City to Windy City



13 Nights

Tour Type

Specific Tour

Group Size

40 people




Following the success of this tour last year…we have decided to do it again, but this time in reverse!

Join Travelling Time on another exclusive one of a kind Music Themed Holiday!  With no long bus journeys, you have more time to enjoy yourself! This fun-filled, value for money tour is not to be missed!


If you want unforgettable memories and great value for money,  join us on this musical journey from Nashville Tennessee to Chicago Illinois. 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.

By joining one of our exclusive tours, you will enjoy short journeys between towns and cities in a comfortable vehicle suitable for your group size. Both your knowledgeable driver and a member of the Travelling Time Team will be on hand to provide a deeper understanding of the landmarks and make sure that your trip is as enjoyable as possible. You wont have to study maps or use navigation systems – as you will travel around as our distinguished guest : exactly as you deserve!
A combination of perfectly planned sightseeing trips, live music experiences, fantastic attractions and loads of free time to explore the wonderful towns and cities you visit – make Travelling Time’s Tours the best way to see the USA!

Visit Nashville Tennessee (4 Nights) Franklin Kentucky (1 Night) Louisville Kentucky (2 Nights) Cleveland Ohio (2 Nights) Detroit Michigan (1 Night)  Chicago Illinois (3 Nights)

Windy City to Music City – 13 Nights (Plus one in flight)


  • 4 Nights Nashville Tennessee
  • 1  Night Franklin Kentucky
  • 2 Nights Louisville Kentucky
  • 2 Nights Cleveland Ohio
  • 1  Night Detroit Michigan
  • 3 Nights Chicago Illinois


  • Coach travel from Nashville to Chicago
  • Travelling Time escorts and local guides
  • Welcome Meeting at Hotel


  • Daily breakfasts
  • 2 Group Dinners – in well-known venues


  • A night at “Kingston Mines”
  • Visit the Green Mill and other Chicago Night Spots
  • Visit Hitsville USA and Detroit Music Scene
  • Slippery Noodle Inn in Circle City
  • The Everly Brothers Musem – Central City
  • Blue Grass Museum Owensboro
  • National Quilt Museum Paducah

and… a few Travelling Time Surprises along the way!


All Travelling Time Tours are designed so you can easily extend your stay in the USA. Call us to discuss your options.

  • Extra Nights in Nashville before the tour
  • Extra Nights in Chicago after the Tour
  • Add on Overlapping Tours
  • Mountains & Moonshine (Before)
  • Midwestern Melodies & DC (After)
  • Pick up a car or a plane and do your own thing!

 All of our tours have limited availability – You can secure your place(s) on “Music City to Windy City” for next year or beyond with a £200pp Deposit – Just call us on 01738 643737 or email us at
Alternatively, you can book and pay in full online today, just choose your preferred departure date below.

All Prices are based on 2 people sharing, A single supplement will be applied at checkout.

Music City to Windy City

Music City to The Windy City – Enjoy the Music and Culture of these wonderful cities and all points in between…Another wonderful music themed tour from Travelling Time!

*Travelling Time are pleased to take private group bookings for Music City to Windy City. If you are booking for your group – and our schedule departure dates do not suit – please call our group department to check the availability of alternative dates. (Minimum group size 8)

Please see the full day by day Itinerary below…

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Day 1 - Nashville Tennessee
Day 1 - Nashville Tennessee

Welcome to Music City USA! Once you are checked in - feel free to join us at the hotel bar for a welcome drink and to meet your fellow travellers.

Day 2 - Nashville Tennessee
Day 2 - Nashville Tennessee

Discover why Nashville the, capital of the U.S. state of Tennessee is called Music City USA! Visit the legendary country music venues which include the Grand Ole Opry House, home of the famous “Grand Ole Opry” stage and radio show. The Country Music Hall of Fame and Museum and historic Ryman Auditorium are Downtown, as is the District, featuring honky-tonks with live music and the Johnny Cash Museum, celebrating the singer's life. You will never run out of things to do and see in Nashville!

Day 3 - Nashville Tennessee
Day 3 - Nashville Tennessee

More free time to enjoy the wonderful music and attractions that can be found in 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, perhaps pop into a couple of the local famous honkytonks - Nashville Palace and John A's Roadhouse can be found in this area. There is shopping at Opry Mills and several restaurants and Madame Tussaud's are here too!

Day 4 - Nashville Tennessee
Day 4 - Nashville Tennessee

On our last day in Nashville - make sure you visit the wonderful Centennial and Bi-Centennial Parks and a visit to the Parthenon (an exact copy - but a couple of inches bigger of course!) is a must. Make sure that you get your cowboy boots and kick your heels on Lower Broadway or Printers Alley tonight - as we get ready to continue our travels tomorrow.

Day 5 - Nashville, Franklin & Bowling Green Kentucky
Day 5 - Nashville, Franklin & Bowling Green Kentucky

As we wave goodbye to Nashville this morning, we will travel North into Kentucky, the Bluegrass State. Our first stop will be the picturesque small town of Franklin with it's lovely courtyard square. Here, we will 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, before heading back to Franklin for dinner and music at the Brickyard Cafe!

Day 6 - Franklin, Central City & Louisville
Day 6 - Franklin, Central City & Louisville

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 in the downtown area enjoying dinner and entertainment.

Day 7 - Louisville Kentucky
Day 7 - Louisville Kentucky

This morning we will take you to The Muhammad Ali Center museum and cultural center which is dedicated to 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.

Day 8 - Louisville, Cincinnati and Cleveland
Day  8 - Louisville, Cincinnati and Cleveland

Today we leave Kentucky and head into Ohio and our first stop is Cincinnati a city on the Ohio River. On our brief visit we will visit the Over-the-Rhine district that is known for its 19th-century architecture and have lunch before travelling to Cleveland. This vibrant city, is home to arts, culture, and landmarks that pay homage to the history of music. From world-class theatre, live music and noteworthy nightlife, you can always find things to do in Cleveland. Made up of "Districts" like Cleveland Heights, Little Italy, Shaker Square and Downtown there are loads fun things to do in Cleveland and we will try to see as much as we can during our two days here.

Day 9 - Cleveland Ohio
Day 9 - Cleveland Ohio

One of the top things to do in Cleveland, is visit The Rock & Roll Hall of Fame and Museum. Once we have paid homage to your favorite music makers, we will take you on a guided tour of the districts!
Later you will have free time to explore at your own pace.
opportunities downtown. You can visit the Aquarium, the Cedar Point Amusement Park or a even Cleveland Metroparks Zoo and Rainforest.

Day 10 - Cleveland, Toledo & Detroit Michigan
Day 10 - Cleveland, Toledo & Detroit Michigan

As we make our way to Detroit today we will stop in the city of Toledo Ohio 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!. Our travels will take us a little bit further around Lake Erie to Detroit - the largest city in the midwestern state of Michigan. The city’s ties to the auto industry, gave it the nickname "Motor City."

Day 11 Detroit, Kalamazoo and Chicago
Day 11 Detroit, Kalamazoo and Chicago

Detroit is the birthplace of Motown Records, whose chart-topping history is on display at their original headquarters, Hitsville U.S.A. We will tour this wonderful museum this morning before we set off for Chicago via Kalamazoo! After lunch we will visit a local brewery before travelling the rest of the way to Chicago Illinois! We will explore a few of best pubs and music venues tonight!

Day 12 - Chicago
Day 12 - 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 few more of the cities fantastic blues clubs!

Day 13 - Chicago
Day 13 - Chicago

On this our final day in the Windy City, we will travel to Navy Pier for a few hours, before heading onto Lake Michigan for a City Skyline Tour. Afterwards, we will spend out last evening in Chicago enjoying a meal and a few drinks together while we listen to some local music!

Day 14 - Tour Ends
Day 14 - Tour Ends

We hope you have enjoyed your time with us, but it is time to say goodbye to your friends...until you see them on the next Travelling Time Tour!


  • All inclusions as per itinerary
  • Travel Insurance
  • Optional Extras
  • Flights

Tour's Location


Based on 1 review
Very Good
A World of Music!

John King


3rd trip with Travelling Time

I had to say that Yvonnevand I love our trips with Lynda & Shawn. This time Chicago to Nashville was great. Next time we are off to Florida with them for the winter...for some well needed heat!
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