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

The next two days are all about exploring ‘The Windy City’. Go down to the Navy Pier, one of Chicago’s most-visited attractions, for a ride on its 196ft Ferris wheel, and walk along its scenic half-mile-long front. Set your sights high on Willis Tower, the third-tallest skyscraper in the Western Hemisphere, and its Skydeck. If you dare, walk over its 103rd-floor glass viewing platform, The Ledge, or opt for a pie in the sky in its restaurant.

Come evening, head below ground to the city’s speakeasies. Filled with sounds of urban blues, these hangouts have hosted many of the greats including Koko Taylor, Willie Kent, Magic Slim and Eddie Shaw. Grab a spot by the stage to be close to the action, or hang out in the back and sip on signature cocktails. But Chicago is more than just blues, it’s jazz too. Spend your last evening in the city at Andy’s Jazz Club. As one of the best-known and most respected clubs in the land, it’s no surprise that the shows come soulful and smooth and the food comes with a choice of steak, fish and salad.

Today, you’ll say goodbye to blues and jazz and hello – or howdy – to country in the genre’s capital Nashville, otherwise known as ‘Music City’. Head back to O’Hare in the early morning for your one-and-a-half-hour flight to Nashville, where you’ll then transfer to your hotel, just two blocks from buzzy Broadway. After a bite to eat at a local distillery or brewery (Nashville has them by the bucketful), we recommend beginning your country journey at the ‘Country Music Hall of Fame and Museum’. Safeguarding over 2.5 million artefacts, you’ll get an education through the ages from Loretta Lynn and Johnny Cash to Dolly Parton and Taylor Swift.

Spend your days in Nashville in some of their best music venues. At the Grand Ole Opry, which has hosted all the big names (think Darius Rucker, Chris Stapleton and Garth Brooks), you’ll be in for a treat as you settle in for an evening performance. Spend your days getting to know the city’s neighbourhoods, such as The Gulch and East Nashville, and their array of street art. If there’s time, we recommend swinging by the Nissan Stadium to watch the Tennessee Titans score a few touchdowns before heading to the historic Printer’s Alley or Broadway (also known as the ‘Honky Tonk Highway’), where you’ll find a plethora of neon lights and bands trying to make it big spilling out of bars. There’s no place like it.

Before heading back to Nashville’s airport to catch your next short-haul flight to New Orleans, fuel up at one of the city’s hot chicken shops. For hot chicken isn’t just a passing trend in Nashville, it’s a way of life. Choose between the OG chicken shack Prince’s or the down-home deli, Big Al’s. Either way, it’s a meal you’ll never forget.

Once at the airport, it’s just a breezy one-and-a-half-hour flight to New Orleans. Another city of many names (‘Crescent City’, ‘The Big Easy’, ‘NOLA’), it has no problem living up to them as you’ll soon find upon arriving at your hotel, where you’ll spend the next four nights. Located in a former 19th-century warehouse, complete with a coffee shop, cocktail bar, gallery and restaurant, it’s the perfect spot to relax after a day of travelling.

Few cities have a soundtrack like New Orleans. Born from the musical memory of enslaved Africans, jazz and the big band music scene it spawned are integral to the Big Easy. Before hitting its many jazz clubs, use your four nights in the city to wander down Frenchman Street, listening to the brassy blooms of trumpets and trombones and stop by Congo Square for the sounds of cymbals, snares and bass drums bounce off its cobblestones. In between stops for po-boys, gumbo and crawfish etouffee, and walks around City and Crescent Park, it’s to Fritzel’s Jazz Club for a night on the town. As New Orleans’ oldest operating jazz club – open seven nights a week – it has become a mecca for jazz lovers and musicians alike. And trust us, its bench seating and classic dive-bar feel is nothing to go on. Once the music starts and cocktails flow, you’ll see exactly why it’s gone for a back-to-basics no-nonsense approach – the music speaks for itself.

Your last internal flight will see you saying see ya to NOLA and hey y’all to Austin. Leave New Orleans’ Louis Armstrong Airport mid-morning for the one-and-a-half-hour flight to Bergstrom International Airport, where you’ll be picked up by one of our representatives and transferred to your downtown hotel. Entrenched in timeless charm, this historic hotspot is a brilliant vantage point for exploring Austin’s entertainment district and beyond.

A big city with a small-town heart, Texas’ state capital doesn’t take its ‘Live Music Capital’ status lightly. Since the 1960s, this progressive city – an anomaly in Texas – has been a haven for artists, writers and musicians. Disillusioned with Nashville’s honkytonk, artists such as Willie Nelson and Waylon Jennings spearheaded a movement that reworked western and county with an incisive injection of rock’n’roll. So, of course, over your three nights in the city, a visit to a couple of its bars, namely The Continental Club and Antone’s, are a must. For the full Texan experience though, we recommend heading to Stubb’s BBQ. Nestled in the heart of the city’s Red River District, its outdoor amphitheatre isn’t just home to killer sounds, beats and light displays, but barbecue treats such as chopped beef sandwiches and brisket platters. Could this be any more Texan?