Burly, sometimes goateed, and partial to vintage plaid shirts, multi-instrumentalist Ira Sullivan looks like Kerouac’s picture of a rough-and-ready hipster. And his music, which he developed in Chicago in the hard-bopping 50s, still brims with the freewheeling expressiveness that the beat writers sought to emulate in their own rhythms and imagery. Twenty years ago he might’ve come off as a throwback, but these days–after the 80s’ surfeit of glossy, carefully scripted jazz–his low-tech creativity and casual, unfettered virtuosity seem visionary all over again. He always has a route planned when he leads a set–and always veers from it, like a cross-country driver lured at the last second by a roadside oddity. Whitney Balliett’s famous observation that jazz is “the sound of surprise” is especially true at a Sullivan soiree: in the middle of a tune he’ll suddenly lean in to tell his sidemen to skip to another rhythm or even another piece. His adventurousness probably also accounts for his proficiency with both brass and reed instruments. Since trumpets and flugelhorns require a different sort of oral musculature than clarinets and saxes, most musicians stick to one family or the other–but even among the handful of exceptions, none is as exciting a trumpeter, as fiery an altoist, or as brawling a tenor man as Sullivan. Though he makes his home in Miami now, in the last few years he’s taken to prowling small Chicago clubs for weeks at a time, sitting in until all hours, like a 30-year-old up-and-comer instead of a stalwart in his late 60s. This quartet gig presents him in a somewhat more formal setting, but I don’t expect that to cramp his style. Tuesday through Thursday, 8 and 10 PM, next Friday and Saturday, August 13 and 14, 9 and 11 PM, and next Sunday, August 15, 4, 8, and 10 PM, Jazz Showcase, 59 W. Grand; 312-670-2473. NEIL TESSER

Art accompanying story in printed newspaper (not available in this archive): photo/Jeff Lowenthal.