Chicago's Jazz and Blues Clubs Host the Hottest Musical Performers

Music lovers crowd Chicago’s blues and jazz clubs where legendary figures as Von Freeman, Franz Jackson and Eddy Clearwater have played. The city is called the “Blues Capital of the World” for good reason.

The city’s annual Chicago Blues Fest and Chicago Jazz Fest are popular events that take place during the summer. Past performers of the Blues Fest include Ray Charles, B.B. King, the late Bo Diddley, Buddy Guy and the late Koko Taylor while the Jazz Fest shows off Chicago's vast jazz talent alongside national and international artists to encourage and educate a jazz audience of all ages.

Luckily one doesn’t need to wait for the free festivals to enjoy live music in Chicago. Many clubs offer nightly performances 365 days a year.

Green Mill is perfect for those who appreciate live jazz in a very cool, speakeasy atmosphere while Rosa's Lounge lets you enjoy live blues without the unnecessary pretentiousness of a club-like atmosphere.

To expose the younger set to the music, places like the Jazz Showcase invites kids to the Sunday 4 p.m. matinee provided the fans-in-the-making observe the unwritten "no-talking" rule. Kingston Mines offers free or discounted cover to students, members of the military and seniors.

Chicago’s jazz and blues clubs are cozy, dimly lit and have soul. Don’t be surprised if you’re seated alongside one of Chicago’s greats who is enjoying the music on his or her day off or just after finishing their own set.

Souvlaki and live jazz? The two usually don't go hand in hand unless you're at Katerina's where Mediterranean fare is on the menu and some of the hippest jazz, funk, blues, boogie-woogie blues, R&B, classical and world music performers take the stage at this dim and cozy club. Note that if there are two sets during the evening, you will have to pay two separate covers. It's easy to walk or drive by this place and wonder if it's any good. Don't make the mistake of not stopping in. It's conveniently located right off the Brown CTA line so it's easily accessible from the Loop. ((773) 348-7592)

The Underground Wonder Bar
Established in 1989, this tiny venue is open 365 days a year, and Lonie Walker, who founded the place, still plays three nights a week. Live music is offered nightly to an incredibly eclectic group of patrons. Jazz and blues are the main focus, but acoustic guitar and piano music are often featured, as are friends who hop on the makeshift stage. It's also one of the few places one can enjoy live reggae. The limited size doesn't allows performances to be very interactive (unless you want to dance between the bar and some tables). Ordering or bringing in carryout food is acceptable. Truly a classic. (312-266-7761)

It's tiny, a bit dingy and crowded. In other words: the perfect place to see live blues. The walls are covered in history of blues and Chicago icons and small tables bring you up close and personal with others, one of whom might be a blues artist having a drink on his or her day off. The club features both obscure and well-known local artists (think Otis Clay and Magic Slim) but it focuses primarily on local talent. Testing your blues trivia here would really be a test because the slightly older crowd consists almost exclusively of aficionados. Shows are highly interactive and CDs of nightly and past performers are for sale. (773-528-1012)

Kingston Mines
This spot's mantra ("Hear the music, drink booze and talk loud") is strictly enforced. With two stages and the only 4am-liquor license among Chicago's blues clubs, Kingston Mines is packed nightly. Local blues and jazz artists often stop by here after their sets at other clubs. With over 46 years of operation, the club recently expanded and now includes three storefronts and a late night kitchen. Kitchen serves up everything from burgers to New Orleans style BBQ ribs and Cajunj style shrimp. If you enjoy loud, riotous entertainment, this is the joint. Students, seniors, members of the military and hospitality industry can bypass the $15 cover charge by showing a valid ID. (773-477-4646)

Jazz Showcase
From Dizzy Gillespie on down to Roy Hargove, jazz legends have been playing owner Joe Segal's Jazz Showcase since 1947. The club has moved multiple times over the decades but has settled in comfortably in this acoustically refined South Loop locale. Audiences are reverent (don't even think about talking during a set, or you'll get shushed). Chicago acts play regularly and even big-name tours often pick up local musicians to round out their bands, guaranteeing a devoted local following. Determined to spread the faith to the next generation of jazz fans, the Showcase invites kids to the Sunday 4 p.m. matinee provided the fans-in-the-making observe the unwritten "no-talking" rule. (312-360-0234)

Buddy Guy's Legends
Attempts to appear seedy only partially veil this club's polished interior and yuppies and tourists often show up. The mellow blues joint offers jam sessions on Monday nights and local acts perform Sunday through Thursday. Friday and Saturday showcase national talent. A plethora of memorabilia fills the cavernous room while pool tables and a Southern kitchen that's open till midnight serving sandwiches and po' boys and jambalaya keep patrons satisfied. (If you can't make it to a show, the venue offers lunch.) Despite its touristy reputation, the club is a great place to see live blues in comfort. Parking can be found in pay lots just south or around the corner. (312-427-1190, 312-427-0333)

Andy's Jazz Club
Andy's Jazz Club originally opened in 1951 to entertain the pressman from the city's burgeoning newspaper industry at that time. Today the jazz club features local performers that cover a range of styles from traditional and swing to bop, fusion, Latin and Afro-pop. For those who wish to dine at the full service restaurant with beef tenderloins and duck breast jambalaya on the menu, make reservations in advance unless you don't mind being seated at the bar. Doors open every night at 4pm and first band begins at 5pm. There is a cover (cash preferred) even if you're dining at the restaurant. The club is conveniently located within walking distance of the Magnificent Mile. (312-642-6805)

Blue Chicago on Clark
Blue Chicago on Clark mainly showcases female vocalists who really know how to sing the blues. The mellow and soulful sounds that emanate from this spot are legendary. The room is small, long, dimly lit and tavernesque with a stage at one end. If you need to sit, get there early in the evening to score a stool otherwise you may have to stand. A full bar is on premises, allowing for a drink or two with the show. There is usually a cover between $8-10 a night (depending on the night and performers) but it's totally worth it for some fantastic Blues sounds. (312-661-0100)

Rosa's Lounge
Remember those places where the musicians just want to play to people who love to hear their music? Rosa's Lounge is that kind of place. No frills, just a classic joint to hear great live blues without the unnecessary pretentiousness of a club-like atmosphere. Visitors grab a drink and let themselves enjoy the music and the diverse crowd that flocks to this place to hear the likes of Sugar Blue and Billy Branch & the SOB. There is a cover charge and full service bar to meet guests' needs (no drink minimum). Tony, the friendly owner who named the place after his mother who helped him open the club, still takes care of his guests every night. (773-342-0452)

Green Mill Cocktail Lounge
Trendy folks and jazz aficionados regularly flock to this cool joint. Once a hangout of Al Capone, Charlie Chaplin and Gloria Swanson, the place has tons of character. It was also a speakeasy during Prohibition, meaning that Green Mill retains a past-days air of the Roaring '20s. Swing music is offered Tuesday and Thursday, Wednesday night is their gyspy jazz band although jazz crops up almost nightly, and Sunday features poetry slams. Cocktails are inexpensive but if you want to enjoy them from a table, get there early and definitely before the bands go on otherwise you'll be out of luck because this place gets packed. (773-878-5552)

Megy Karydes has spent more than 20 years as a professional writer and most of her life in Chicago. While she’s traveled extensively internationally, visiting each of the 50 states is on her bucket list. An adventure seeker, she’s game for anything from mixed martial arts training to competing in obstacle course races. A self-proclaimed coffee snob and “greenie” who loves farmer-grown food and locally-grown craft beers & wine. She’s yet to find an outdoor beer garden she doesn’t like.  Mixing writing and food/drink is her specialty, especially when it involves travel. To read her work, visit

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Maps and Directions

Katerina's 10Best List Arrow
Type: Live Music, Lounge
Neighborhood: North Center
The Underground Wonder Bar 10Best List Arrow
Type: Live Music, Lounge
Neighborhood: Magnificent Mile
Kingston Mines 10Best List Arrow
Type: Dance Club, Late Night / After Hours, Live Music
Neighborhood: Lincoln Park
Jazz Showcase 10Best List Arrow
Type: Live Music, Lounge
Buddy Guy's Legends 10Best List Arrow
Type: Live Music
Neighborhood: Printers Row
Andy's Jazz Club 10Best List Arrow
Type: Late Night / After Hours, Live Music
Blue Chicago on Clark 10Best List Arrow
Type: Live Music, Nightlife District
Rosa's Lounge 10Best List Arrow
Type: Live Entertainment, Live Music, Lounge
Neighborhood: Logan Square
Green Mill Cocktail Lounge 10Best List Arrow
Type: Late Night / After Hours, Live Music, Lounge
Neighborhood: Uptown
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