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.

AFTER-FEST SESSIONS AT JAZZ SHOWCASE

The after-fest jam sessions at Joe Segal’s Jazz Showcase are such a tradition by now that one can hardly believe Segal used to close his club (then in the Blackstone Hotel, steps from Grant Park) completely during the Jazz Festival, on the grounds that he couldn’t compete if they were giving it away down the block. Now a bit savvier (if farther from the fest site, at 59 W. Grand), Segal knows how to lure listeners who want more music–or like it served at tables. He’ll spend each afternoon at the Petrillo sound checks, inviting or cajoling festival headliners to drop by. Then around 9:30 each night all he has to do is set a rhythm section in motion behind an engaging leader and wait.

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.

AFTER-FEST SESSIONS AT HOTHOUSE

Located less than a block from the old Jazz Showcase, HotHouse (31 E. Balbo) rarely gives its stage over to out-and-out jam sessions; instead, the club lines up acts that fill holes in or augment the Grant Park offerings. Jazz Fest rarely includes blues pianists anymore, but for Thursday night HotHouse has booked a bevy of boogie-woogie ivory ticklers–the wonderful Erwin Helfer, Barrelhouse Chuck, and Detroit Junior, plus former Uppity Blues Woman Ann Rabson and the legendary Pinetop Perkins. If you enjoy Friday’s fest set by trombonist Ray Anderson’s quartet you’ll want to catch Edward Wilkerson Jr.’s 8 Bold Souls, a band that similarly mixes tradition and deconstruction (but on a scale twice the size), Friday night; they’ll be joined by veteran free improviser Oliver Lake, who plays Grant Park the following evening.

On Saturday from 3 to 6 HotHouse gives listeners a glimpse into how the sausage gets made, hosting a free open rehearsal by the NOW Orchestra (who play Petrillo on Sunday night), conducted by composer and trombonist George Lewis. Saturday night the unsinkable Roscoe Mitchell–creator of the band that became the Art Ensemble of Chicago, and a tireless experimenter and saxophone scientist in the three decades since–leads a set that starts with his quartet and promises to embrace other noteworthy performers. And Sunday night, after a fest appearance with the band Sphere, the lively and urgent alto saxist Gary Bartz will hook up with another of his regular gigs–the Freebop Band, led by Chicago trumpeter Malachi Thompson, who in two recent performances played with a fire and precision missing from his music for the better part of a decade.

AFTER-FEST SESSIONS AT THE VELVET LOUNGE

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.

In free-for-all sessions on Saturday and Sunday nights, the rhythm section comprises guitarist Jeff Parker, bassists Tatsu Aoki and Malachi Favors, and drummer Hamid Drake, and, as he has every year for the last decade, the ageless New Orleans free-jazz saxist Kidd Jordan will join in. In the past, guest artists like trombonist George Lewis (a big presence this year at the fest) and saxman Douglas Ewart have turned in some ferocious performances; this year look for trombonist Ray Anderson and saxophonist Oliver Lake, among others.

SOUTHPORT ARTISTS AT POPS FOR CHAMPAGNE

This year marked the 25th anniversary of Southport Records, the brainchild of pianist Bradley Parker-Sparrow, born near Cabrini-Green (where Sparrow had his first studio), then nurtured by Sparrow and his wife, vocalist Joanie Pallatto, in more hospitable surroundings at Southport and Cornelia. An outgrowth of Sparrow’s own recording career and his interest in sound engineering, Southport sometimes reflects the couple’s quirky tastes–but just as often they release finished albums brought to them by local artists who wouldn’t otherwise get heard. Their catalog now tops 100 releases, and the hits far outweigh the misses.

Southport offers a three-night slate of after- and during-fest sessions at Pops for Champagne (2934 N. Sheffield), heavy on piano and vocals in deference to the room’s polite ambience (and booming acoustics). Thursday at 8:30 the sweet-voiced Linda Tate–a rarely heard singer with two albums on the label–appears with pianist Bobby Schiff and bassist Jim Cox. Schiff returns Friday evening at 5:30 to present 11-year-old vocalist Susan May, after which pianist Ron Surace–a solid improviser with a deceptively light touch–leads a terrific trio with bassist Tatsu Aoki and drummer Dave Pavkovic. Saturday night around 9 Sparrow and Pallatto present their Machine Band, as heard on We Are Not Machines, a concept album about the homogenization of American culture that includes a track called “Cut Off the Head of Eminem and Stick It Up His Butt!”–not exactly dinner music.

JAZZ TROPICALE CRUISE ABOARD THE TALL SHIP WINDY

Among the various projects that make Marshall Vente the busiest man in Chicago jazz is Tropicale, his homage to Brazil, which features the Rio-born vocalist Rita Duarte and her countryman, drummer Luiz Ewerling. The music offers suitable accompaniment to lake breezes and moonlight; on Friday count on the former (the moon will actually be in its last quarter) when Vente hosts one of his “Jazz Tropicale” cruises aboard the tall ship Windy. The schedule’s tailored for Jazz Fest: Windy will leave her Navy Pier berth at 10 PM for a two-hour sail on Lake Michigan, allowing just enough time for festival patrons to hear the last notes in Grant Park, grab a cab, and hop aboard. In addition to Tropicale, the lineup includes harmonica virtuoso Howard Levy and Two for Brazil, the sprightly duo of saxist Greg Fishman and Brazilian guitarist and vocalist Paulinho Garcia. Tickets are $50 and reservations are recommended; call 312-595-5472.

DELMARK ALL-STARS JAZZ BRUNCH

Eight years ago, the folks at Jazz Record Mart (444 N. Wabash)–exhausted from running the store all weekend, selling music at the festival each night, and barely having a chance to eat–decided to combine business with bagels in the Delmark All-Stars Jazz Brunch. As in years past, it runs from 10 AM to noon on Sunday. The store provides a small mountain of fresh fruit, plenty of bagels, juice, coffee, and pastries, and live music courtesy of Delmark Records (which, like the Mart, belongs to 50-year music biz veteran Bob Koester). The lineup runs the gamut from clarinetist Norrie Cox and his New Orleans Stompers, a superb trad band that’s just released a new disc, Live at the Illiana, to modernists like drummer Hamid Drake and saxists Fred Anderson and Ari Brown. Also on the program: composer and saxist Ernest Dawkins, the AACM stalwart whose widely heralded New Horizons Ensemble recently recorded at HotHouse for an upcoming Delmark release; twentysomething tenor sensation Frank Catalano; bassist Tatsu Aoki; drummer Al Green and saxist Othello Anderson, whose quintet has just released its first album, Mr. Lucky; and trumpeter Malachi Thompson (see HotHouse listing above).

AFRICAN FESTIVAL OF THE ARTS

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.

Highlights of the schedule include blues and world-music legends as well as some noteworthy jazz artists. On Friday, Gnawa innovator Hassan Hakmoun (see Spot Check) takes the stage at 4 PM, followed by jazz-pop-funkster Roy Ayers (7 PM) and Brazilian pop star Daniela Mercury (8:30; see Critic’s Choice). Saturday night 72-year-old R & B legend Bobby “Blue” Bland plays at 6:30, with keyboardist-producer George Duke slated for 8:30. Sunday’s schedule includes vocalist Rachelle Ferrell (6:30)–with her freakish high register, she’s jazz’s answer to Minnie Riperton–followed by conguero Poncho Sanchez and his band; Monday offers Malachi Thompson’s Africa Brass with guest saxist Gary Bartz (2:30), South Africa’s Mahotella Queens (5:30), and fabled funkstronaut George Clinton (at 7).

Art accompanying story in printed newspaper (not available in this archive): photos/Michael Jackson, Darlene Martin, B.P. Sparrow.