The Chicago Jazz Festival is among the world’s longest-running outdoor events: at 24, it’s older than some of its attendees. But not until the late 80s did the festival begin its transformation into the citywide free-for-all it is today, with club owners, record-shop managers, and cultural institutions all looking for ways to share the wealth of talent that descends on Chicago (and emerges from its holes-in-the-wall) for the weekend. Nowadays the wide array of ancillary events, which range from early-morning brunches to late-night jam sessions, means there’s hardly a waking moment when you can’t find some jazz going on. Many of the happenings highlighted here complement the Grant Park offerings; some will provide second helpings for performers and fans whose appetites have only been whetted by the short sets and tight scheduling at the park.

This year’s house band features the usual suspects: piano powerhouse Willie Pickens, bassist Marlene Rosenberg, and drummer Robert Shy, behind expat Chicagoan Ira Sullivan, who travels with trumpet, tenor and soprano saxes, flute, and sometimes alto sax–which means whoever else shows up will find at least one complementary ax. Segal has already confirmed appearances by guitarist Larry Coryell, tenor men George Coleman and David Sanchez, pianist Danilo Perez (all of whom have headlined at the Showcase during the last year and a half), and baritone saxist Claire Daly; don’t be surprised if altoists Miguel Zenon (of Sanchez’s band) and Arthur Blythe show up as well, and keep your fingers crossed for down and dirty rice-and-beans drummer Idris Muhammad.

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Even after it became the nexus for Chicago’s free-music renaissance in the 90s, Fred Anderson’s Velvet Lounge (21281/2 S. Indiana) maintained its daytime profile as a workingman’s bar, and when Anderson–an original member of the AACM and a latter-day legend of avant-garde jazz–isn’t holding forth on the stage, he’s still pouring the drinks. The after-fest jams hosted by him and his quartet are always a highlight of the weekend.

JAZZ TROPICALE CRUISE ABOARD THE TALL SHIP WINDY

It began 12 years ago as a small fair; now the African Festival of the Arts has grown into a major-league Labor Day event. It features the expected crafts, but also a fine-art show, a “weaving village,” a fashion parade, the Hyde Park Chess Tournament, and an Afro-Caribbean food court–as well as an array of music that spans the diaspora and sometimes gives Jazz Fest some stiff competition. It runs Friday through Monday from 10 AM to 10 PM at Washington Park, 55th and Cottage Grove, and runs $8 per day, or $5 for preteens and oldsters. A four-day pass sells for $25.