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Discovering jazz in the Windy City

BY Simon Button

5th Dec 2019 Travel

6 min read

Discovering jazz in the Windy City
Simon Button investigates the exhilarating jazz scene and its history in the Windy City
Cutting his teeth as a jazz singer for Tommy Dorsey’s big band in Chicago in the late 1940s, New Jersey-born Frank Sinatra adored the city so much he returned time and again as a solo artist. He also went on to sing its praises not once but twice, landing himself two signature tunes; a 1957 cover version of the 1920s standard "Chicago (That Toddlin’ Town)" and declaring it to be "My Kind Of Town" seven years later.
It’s no wonder this Louis Armstrong fan would be drawn to a city where Armstrong himself had journeyed from New Orleans in 1922. When Louis got there as a wide-eyed musician following in the footsteps of his mentor Joe “King” Oliver, the trumpeter extraordinaire found the joint to be jumping and, although much has changed in the subsequent near-century, it still is.
Alexander skyline
My visit to the Windy City (thus nicknamed not, apparently, because of the breeze that blows in off Lake Michigan but because of the hot air spouted by politicians bidding to host the 1893 World’s Fair) is timed to coincide with the annual jazz festival as a starting point to explore where the genre is currently at in the place that helped put it on the map.
The Blackstone Hotel is my bolthole for the first three nights and it proves to be elegant and beautifully furnished, with huge rooms, a stunning lobby where President Truman used to play the piano, a breathtaking ballroom that was used in The Untouchables movie and a basement barbershop where Al Capone got his hair cut.
Freddy Cole
The hotel is also steeped in music history, having played host to the likes of Lena Horne and Nat King Cole—which ties in nicely with my first visit to the 41st Annual Chicago Jazz Festival in Millennium Park, where the opening night headliner is Freddy Cole, playing an emotional tribute to his late brother in the huge outdoor Jay Pritzker Pavilion.
Prior to the concert I take in a stirring performance by veteran trumpeters Pharez Whitted and Corey Wilkes at the Cultural Center, then sit down for a chat with 59-year-old Whitted—who has played with everyone from George Duke to The Temptations and who, through his work for youth programmes, is one of the locals helping keep the musical genre alive and well.
chicago bean.jpg
“This is one of the most important cities in the evolution of jazz,” he tells me, “because it is where many of the jazz musicians from the South ventured to first.”
Jazz’s roots date back to the late 19th century in New Orleans; a fusion of blues and ragtime which soon caught on in Chicago too, firstly in the black neighbourhoods before eventually crossing over into the mainstream. Armstrong moved to the Windy City during the Great Migration of African-Americans from the South, many of whom were musicians poised to take advantage of Chicago’s flourishing jazz scene, where it evolved into a more freeform, improvisational genre.
Pharez laments the loss of intimate clubs (like Katerina’s and Bucket O’Suds) and the scene’s sense of community, saying: “Musicians used to hang out more and share ideas, but you don’t see that as much today.”
lousi armstrong
Purists may also lament the fact that the one-time underground genre has lost some of its cool, with concerts in big venues like the Symphony Center and the Pritzker Pavilion attracting the sort of upscale crowd you’d never find in snugger nightspots. But the jazz concert as event is nothing new; Chicago’s very own Benny Goodman played New York’s Carnegie Hall as far back as 1938. And the free-for-all jazz festival has smaller satellite stages and citywide events, and there are still plenty of joints and dive bars.
"Jazz isn’t boring at all"
Pharez is happy to see jazz being played out across all entertainment platforms. “Small spaces, clubs, theatres, festivals—it’s all good,” he smiles.
And he’s thrilled to be joined on stage by 18-year-old upright bass player Micah Collier, who is a brilliant musician as well as a young ambassador for jazz. “A lot of young people aren’t hip to it and they think it’s old-school music for the older generation,” says the native Chicagoan, “but for me it’s all about freedom. It’s about expressing yourself and having a simultaneous conversation with others on the bandstand.”
Some of Micah’s sports-minded friends were sceptical at first. “But over time they’ve come to gigs and they’re like, ‘Oh, jazz isn’t boring at all’,” he grins.
The next day I hop on a bus for the "Chicago Crime Tour," which sounds cheesy but actually turns out to be really informative. Mobsters, prohibition and jazz went hand-in hand in the 1920s and 30s, with bootlegger and mob boss Al Capone booking musicians for his numerous illegal speakeasies such as the long-standing Green Mill Cocktail Lounge.
"Appreciation is appreciation. The important thing is the music."
When I visit the Green Mill that night I’m happy to discover it’s still very much the dive bar depicted in the 1957 film The Joker Is Wild—in which Sinatra (no stranger to the Mob, of course, although he always denied any direct connection) played the singer Joe E Lewis, who had his face slashed and throat mangled when he refused to perform at the uptown venue.
green mill coktail lounge
Today it attracts a boisterous crowd, whose banter doesn’t seem to bother jazz organist Chris Foreman—a Friday night fixture at the Green Mill who tells me between sets: “People are here to listen and they’re also here to talk. I give them room to do both.”
Blind since birth and now in his early sixties, Chris is cheered by the fact “more young people are coming to shows and there are more young musicians”, and like Pharez he’s not a snob when it comes to where fans get their jazz fix. “Appreciation is appreciation. The important thing is the music. It’s about personal expression and it’s unique in that everybody has their own voice.” He laughs. “I’m still working on mine.”
The following morning I do the Architecture Center’s "Historic Treasures Of Chicago’s Golden Age Walking Tour," which takes in such stunning sights as 1920s Art Deco masterpiece Carbide & Carbon Building (designed to look like a prohibition-defying champagne bottle) and the breathtaking lobby of the Palmer House hotel.
The Palmer Hotel is my place of residence for the last two nights of my visit and it’s hallowed ground for jazz enthusiasts, since it was in its legendary Empire Room that Sinatra first sang with Dorsey’s orchestra and such icons as Armstrong and Ella Fitzgerald performed.
Palmer House_History is Hott.jpg
The guest rooms are a bit dated but they’re nicely quiet compared to the always-buzzing Lockwood bar and restaurant (which serves hearty breakfasts and amazing lobster rolls) and you really do feel you’ve gone back in time when you stay there.
After checking in, I spend the evening at Andy’s—a former saloon that was refashioned into a jazz bar in the 1970s and has been nicely retro-styled to look like a joint from 50 years earlier. Mellow-voiced vocalist Stephanie Aaron could have hailed from another era too as she sings such classics as "Night And Day" and "Tea For Two" to an attentive crowd.
The next day I sample the jazz brunch at Le Piano, a one-time cabaret theatre in the upscale East Rogers Park neighbourhood that reopened as a club just a few months ago. It turns out to be an eclectically-furnished bit of jazz heaven, fashioned around a beautiful grand piano that sits proudly in front of the windows.
frank sinatra.jpg
A fixture on the Chicago scene for three decades, co-owner and pianist/drummer Chad Willetts has reservations about bigger, more formal venues, saying: “They drive new audiences but there’s a big distinction between a jazz club and an event space. The latter is more of a controlled format, where no-one talks and it’s a beautiful performance. But there’s no spontaneity in that.”
The author enjoying a "Happy Ending" at the Le Piano club 
It doesn’t get much more spontaneous than downing a few cocktails, then lying beneath the piano—which is exactly what I do on my last day. But I’ve not drunk shamefully myself under this grandest of instruments; it’s the club’s novel $10 "Happy Ending" where guests get a whole new aural experience. As the sound of "Pure Imagination" wafts over my head, I wonder what Armstrong or Sinatra would have made of such a gimmick but it’s a thrilling, deeply moving experience that makes me feel Chicago is very much my kind of town too.

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