Start with Andy's Jazz Club in River North. A rotating list of excellent local players split up the week with several shows every night. You'll never get stuck in one groove with groups like the Windy City All Stars. The room is friendly, with close, clear sightlines throughout.
Not far, at Pops for Champagne you can sip on some decadent bubbly to the tune of live jazz. In the chic lounge, nibble on small plates, cheeses and desserts while musicians play to the polished crowds every evening Sunday through Tuesday.Or head to the South Loop to Jazz Showcase. Chicago's most nomadic jazz club is also one of its finest, especially with its new digs on South Plymouth Court in historic Dearborn Station. Owner Joe Segal opened the original in 1947 and he still comes out to thank you too. When talented players come to town, this is typically their first stop - the who's who of the jazz world that have passed through the doors include Dizzy Gillespie, Thelonius Monk and Bud Powell.
Also in the area, Reggies Chicago is the music fan's ultimate dream, combining a laid-back music joint alongside a bar and grill, a kickin' rock club, a roof deck that also host performances and a record store -all in one space. Here the décor is delightfully irreverent, filled with a mess of memorabilia and bold accents that complement the rockstar waitstaff, and the diverse crowd reflects the even more diverse musical bookings, which besides jazz covers everything from punk, metal, folk, blues and hip hop.
If martinis and a quiet scene are more your style, be sure to stop into the contemporary M Lounge. A sleek bar, dim lighting, inviting couches and velvet curtains set the scene for live jazz at least twice weekly while a traditional and modern jazz soundtrack plays on other nights.
However, no tuneful tour of our town is complete without a pilgrimage to the Uptown haunt Green Mill. Its past reaches back to the Roaring Twenties, when jazz hid behind closed doors. Anyone who's ever played a syncopated note has played there. You might even hear superb local talent like Victor Goines (Director of Jazz Studies at Northwestern University) or Father John Moulder (a guitar-playing parish priest) hop up on stage for a little jam.
And if you're lucky enough to be in town for the Chicago Jazz Festival over the Labor Day holiday weekend, the city will bring all this great talent together and more. A neighborhood alternative, the Hyde Park Jazz Festival is a South Side show-stopper as well later in September each year.