Chicago should be on the bucket-list of every music lover

This legendary American city was built on music, and is the perfect place to shake a tail feather.

Tamara Hinson

4 min read

September 27, 2024 - 4:56PM

Lifestyle

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Reminders that Chicago is a city built on music are everywhere, whether it’s Slate Street’s towering mural of guitar-strumming blues legend Muddy Waters, incredibly talented buskers serenading commuters or music-themed monuments such as Grant Park’s Spirit of Music, which honours Chicago Symphony Orchestra founder Theodore Thomas.

Then there is Bronzeville, the neighbourhood where I find the late jazz pianist Nat King Cole’s house on a quiet leafy boulevard. The home is now privately owned, although a Chicago Tribute Marker – used to identify historical buildings – stands on the sidewalk. Bronzeville is at the heart of Chicago’s African-American community, and its connections with music run deep. The late blues musician Muddy Waters once lived here, jazz supremo Louis Armstrong had a second home here, and it’s close to the Walk of Fame – a trail of pavement plaques dedicated to those who left an indelible print on Chicago. Many are musicians.

It’s hardly surprising that some of the world’s most talented musicians based themselves in Chicago, nor that many are still here. Take Louisiana-born Buddy Guy, who moved here in 1957. His biggest fans include Eric Clapton, Jeff Beck and Rolling Stones bassist Bill Wyman, and he regularly performs at his Chicago blues club, Buddy Guy’s Legends. Sadly, he’s not on stage when I visit but it’s everything a blues club should be: chequerboard flooring, an intimate stage with a backdrop of exposed bricks, and walls lined with memorabilia, including Jimi Hendrix’s shoes.

Another essential stop-off for music fans is the House of Blues. Near the entrance, visitors can pose on a bench between statues of the Blues Brothers (the 1980 movie was set in Chicago). Inside there are multiple venues (the restaurant and bar, with its small stage and abundance of blues-themed artwork, is my favourite) and in the lobby, busts of legends who’ve performed here peer down at me – people like Otis Redding and Big Joe Williams, known for the distinctive sound of his nine-string guitar.

While Chicago is built on blues, it’s also one of America’s most musically diverse music cities, proof of which is Wicker Park, a proudly unpolished neighbourhood filled with independent record shops and vintage clothing stores. In the Wormhole Coffee, walls are covered with posters for gigs by local bands, and the retro treasures displayed like priceless paintings include a ghetto blaster. The cafe’s playlist reflects Chicago’s diversity – one second I’m being serenaded by Dolly Parton, the next it’s a weirdly addictive mash-up of drum ’n’ bass beats layered over saxophone riffs.

Buddy Guy regularly performs at his Chicago blues club. Picture: Alamy.

Neighbouring businesses include Reckless Records, where music fans come for signings and in-store performances. I spend a happy hour browsing the aisles, resisting the temptation to splurge on rare vinyl or limited-edition Thin Lizzy action figures.

Chicago is also famous for its jazz. Al Capone, who spent much of his life here and is buried in the Mount Carmel Cemetery, just outside the city, loved to hang out at the Green Mill, a jazz club once part-owned by fellow mobster Jack “Machine Gun Jack” McGurn. The club is still going strong, and one of the most popular booths is by the door – Capone, weary of attempts on his life, wanted to see who entered (though it was syphilis that helped kill him in the end).

My most unexpected musical revelation comes at the National Museum of Mexican Art, which regularly hosts exhibitions about Mexican immigrants’ impact on Chicago’s music scene. My visit coincides with the Mariachi Potosino: The Sound of Home exhibition (which runs until mid-October). It focuses on José Cruz Alba, who arrived in Chicago from Durango, Mexico and founded the city’s Mariachi Potosino band in 1958. José introduced mariachi music not only to Chicago, but the mid-west. In Chicago, his band serenaded mayor Richard Daley in 1963, Robert F Kennedy in 1965, and Richard Nixon in 1973.

Al Capone loved to hang out at the Green Mill jazz club, which is still going strong. Picture: Tamara Hinson.

I’m quickly learning that Chicago is a great place to fall in love with unfamiliar genres. Even my hotel, the Marriott-owned W Chicago City Centre, is in on the act, hosting rising artists in its Midland Social Club, a beautiful bar with 1928 Beaux-Arts architecture which evokes the swanky jazz clubs of Capone’s era.

I finish my music-themed exploration of Chicago at the Briny Swine Smokehouse & Oyster Bar. I’ve heard great things about that night’s entertainment – local blues act Smiley Tillmon Band. Georgia-born Smiley shares the spotlight with bassist Tom Rezetko, drummer George Baumann and Kate Moss – not the supermodel but a ridiculously talented blues guitarist.

Tillmon, it seems, is one of Chicago’s busiest blues musicians. “I arrived in Chicago in ’62 and I’ve been workin’ here ever since,” he tells me. His love of the city is clear, although he has concerns about the direction the music industry is heading. “The incentive to make music is lower now – people can steal your work. I’m okay – I just worry about the young ones.”

I finish my music-themed exploration of Chicago at the Briny Swine Smokehouse & Oyster Bar. Picture: Jeff Schear Visuals.

I’m shocked when Smiley tells me he’s 85, although I can’t see him retiring any time soon, despite his packed schedule.

“I take a lickin’ but I keep on tickin’,” he says with a smile. By the end of the night, I’ve fallen totally in love with Chicago. And Smiley has introduced me to his daughter, serenaded me at my table and dedicated at least two songs to “Tamara Hinson from London”. And maybe, in another life, from Chicago.

The writer was hosted by the W Chicago City Centre.