Over Labor Day weekend, the Bean hosted a surprise daily ritual. In the late afternoon, tourists gazing at the sculpture would be pulled away from their selfies by the raucous sound of a second-line band. The Windy City Ramblers — led by the bouncy trumpeter Mario Abney and, sometimes, his two pint-sized kids — would then process into Pritzker Pavilion. Throngs would follow them, like jerseyed Pied Pipers. Don’t be shy, the procession seemed to say. This is where you should be.
Welcome to the Chicago Jazz Festival, on locals’ calendars but often a happy discovery for the many holiday-weekend visitors who descend on our city. Those who stuck around Pritzker Pavilion got a primer in jazz and its many strains: its early days, embodied by reedist Natalie Scharf, stride pianist and singer Paul Asaro, and four pairs of swing dancers (Sunday); more New Orleans greatness, via trumpeter Kermit Ruffins and his Barbecue Swingers (Saturday); and otherworldly vocal talent, like operatic countertenor-turned-jazz-singer G. Thomas Allen (Sunday).
On a very autumnal weekend, the festival also transported listeners to the sunny Caribbean. I can think of only one other musician who is as young at heart as Jamaican pianist Monty Alexander, 81: Herbie Hancock, who himself turned 80 this year. Alexander pulled out a baby-blue melodica to lay down a filthy ska rhythm for his band. As he had during 2023’s Ramsey Lewis tribute, Alexander paid homage to fellow countrymen Bob Marley and Harry Belafonte, sneaking in snippets of “Day-O” all set long. Later, he ignited the crowd when he brought out Weather Report drummer Bobby Thomas Jr. as a special guest.
Between Irakere at Ravinia and the Buena Vista Social Club’s Eliades Ochoa as a festival closer, it’s been a great summer for Cuban jazz. Like danceable sendoffs of yesterday, Ochoa brought the audience to its feet for Buena Vista classics like “Chan Chan” and “El Cuarto de Tula.” But he also included a heap of originals from his 2023 album “Guajiro,” starting with “Vamos a alegrar el mundo.” That they did.
If you want to be in Ochoa’s band, you’d better be at the top of your instrumental game and be able to sing. Bassist and singer-songwriter Esperanza Spalding must share that prerequisite. The members of her crack band — multi-instrumentalist Morgan Guerin, drummer Eric Doob, and guitarist Matthew Stevens — backed her voice with lush three-part harmony.
What a voice it is, and has been. Like the rocket-ship earrings she wore on Thursday, Spalding can blast off into the stratosphere, whether for ornamental effect in “Thang (Hips)” or to literally scream, as in her space-age riff on “I Want It Now” from the 1971 “Willie Wonka and the Chocolate Factory.” (And kudos to Spalding for using her last moments on the Chicago Jazz Fest mic to shout out the 60th anniversary of the Association for the Advancement of Creative Musicians — oddly muted in this year’s celebrations, save Pavilion slots for saxophonists Ari Brown and Ernest Dawkins.)

