Jazz music in The Windy City is a different kettle of fish. Chicago jazz is an eclectic mix of Mississippi Delta (the area between the Mississippi and Yazoo rivers) and the New Orleans’ ‘Dixieland’ style, a movement kickstarted by the Original Dixieland Jass Band, who made the first-ever jazz recordings in 1917.

If you watch jazz in Chicago be prepared for original pieces, classic covers, and improvised sessions that last long into the night – or even the morning!

The city has seen almost every influential jazz name play a headline act. The Chicago Jazz Festival, still run in Millennium Park, has featured stars such as Sonny Rollins, Ornette Coleman, Jimmy Dawkins, Ella Fitzgerald, and Miles Davis.

King Oliver and Jelly Roll Morton plied their trade in the Chicago music scene, while Louis Armstrong added sophistication to traditional jazz tempos in the mid-1920s, during the Jazz Age. Bud Freeman, Frank Trumbauer, and Gene Krupa formed an important part of a Chicago style so crucial to the genre that keeps inspiring musicians to the modern day.

Let’s dive into the history of midwestern jazz.

The Best Chicago Jazz Clubs

The Green Mill Jazz Club, also known as the Green Mill Cocktail Lounge, is a club in Chicago’s Broadway district. The venue has been featured in many Hollywood films including High Fidelity, The Dilemma, and Chicago Overcoat. It has also been mentioned in Star Trek.

The site with the iconic neon sign, located at Lawrence and Broadway, was opened in 1907. It was named after Paris’ legendary Moulin Rouge club (translated as ‘Red Mill’) but later changed names to avoid association with Chi-Town’s Red Light District.

During Prohibition, “Machine Gun” Jack McGurn, a ranking member of Al Capone’s gang, owned the club. Legend says if Capone and his men saw trouble from the authorities they would escape to the tunnels that are said to lie beneath the bar. Ask the bar if they’ll let you into the trapdoor beneath and the answer is a resounding ‘no’. Al Capone’s favorite booth is preserved as a nod to the past.

The place is as glamorous inside as its neon sign would suggest. Glittering mirrored pillars light up the bar. Post-Prohibition, Al Jolson (known as ‘The World’s Greatest Entertainer’ during the 1920s), Tommy Dorsey, Billie Holliday, and Louis Armstrong performed here.

Nowadays, it is not unusual to witness the latest big names in jazz, closely followed by late-night jam sessions that carry on into the early hours. Such names include Bernard “Pretty” Purdie, Chris “Chrissy Boy” Foreman, and Penn & Teller collaborator Mike Jones.

Bands play from 8 pm-midnight in a cash-only bar that’s open until 1.11 am. No, that is not a typo.

Rumors say it’s also the longest-running jazz club in the country. Just don’t ask about the trapdoor.

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Constellation, just off the city’s charming Roscoe Village, is a performance art space specializing in jazz, improvised and experimental music. The venue seeks to support the city’s burgeoning artist community.

In the former Viaduct Theater, the space was founded as an African-American-focused collaborative cultural location, later tweaked as a nonprofit diverse entertainment platform. Constellation’s president Mike Reed was voted as a “Rising Jazz Star”, having worked with jazz instrumentalist Roscoe Mitchell and avant-garde trumpeter Wadada Leo Smith.

The Constellation fills the gap as a weekend refuge from other locations that have mid-week jazz evenings. If you’re a musician, a slot at the spot is super-accessible and amenable to progressive performance at a scene not unlike many jazz hotspots.

The stage welcomes unrefined acts open to cross-pollination and forming communities straddling the borders of fringe art. Willing to improvise, share ideas, and progress with an audience in full flow? Constellation is for you.

Previous performers have included the Grammy-nominated jazz pianist Fred Hersch and guitarist Bobby Broom.

The performing arts venue is also generously supported by the Illinois Arts Council and the Chicago Department of Cultural Affairs and Special Events, amongst others.

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The Jazz Showcase is the oldest historic jazz showcase venue in Chicago, located in the city’s diverse South Loop neighborhood. Until his death in 2020, Joe Segal was the first man you met at the door, having run the club since its opening in 1947. The Jazz Showcase is now owned and operated by his son, Wayne.

The list of previous performers reads like the very best of American jazz music. Count Basie, Sun Ra, Art Farmer, Herbie Hancock, Hank Crawford, and Rahsaan Roland Kirk have all played at the venue, amongst countless others. Dizzy Gillespie also played the Jazz Showcase on his birthday for many years.

It’s known for its 4 pm Sunday Matinee performances, aimed at families. Jazz is performed seven days a week, with exclusive 8 pm and 10 pm slots.

The Showcase was formed through the owner Joe Segal’s love for attending jazz performances in the city’s famed jazz hotspot Randolph Street. In 1957, Segal set up the Showcase as a permanent floating jazz club with an estimated 63 different locations over the years.

It endured due to the owner’s insistence that Chicago must have a place for jazz to thrive. Yet it was at a considerable financial cost. Word has it that Segal used to occasionally borrow money off the musicians he was hiring to play. Some say the special times lay in the platform’s former residency at South Michigan Avenue’s Blackstone Hotel, where the musicians mingled with fellow guests. Others recall the fun period on North Rush Street.

The current incarnation at South Plymouth Street is a testament to times gone by. Memorabilia and photographs bedeck the walls. The permanent space allows for events such as the annual Charlie Parker Month and four-night shows by the Cyrus Chestnut Trio and Jeremy Pelt Quintet.

The 170-seat venue is professed to be ‘Where Jazz Lives in Chicago’.

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One of Chicago’s most respected jazz venues, Andy’s Jazz Club sits on the city’s East Hubbard Street. Formed in the 1950s as an outlet for The Second City’s newspaper employees, the site did not become a jazz venue until 1977. Traditional jazz promoter Penny Tyler & guitarist John Defauw arrived at the club and proposed showcasing jazz bands at a lunchtime slot.

The first shows were performed no-frills with no stage, lighting, or fanfare. However, the quality of the music showcased saw interest grow. Thus, the ‘Jazz at Noon’ sessions expanded into midweek days and later, permanent ‘Jazz at Five’ and ‘Jazz at Nine’ slots.

The ‘Jazz at Nine’ kickstarted the venue as a cultural jazz hub at the place previously struggling as a shot-and-a-beer joint for journalists needing a post-work release. A new wave of budding Chicago jazz musicians came forward to show their talents at Andy’s, including improvised trumpeter Corey Wilkes and Frank Catalano.

The noon showcase has since been shelved, however, four nightly shows, each at ninety minutes, are prevalent to the current day. The club, located north of the Chicago Loop, is now a Chicago tradition.

Miles Davis’ former sideman Joey DeFrancesco has previously played at the jazz club, so too hard bop saxophonist Von Freeman and former Fats Waller touring musician Franz Jackson.

Current shows include the Late Night Concert Series and back-to-back afternoon sets from established musicians. Andy’s has recently showcased artists such as Mario Abney & The Abney Effect, The Trumpet Summit, and multi-Grammy award-winning artist Brian Lynch.

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Should you find yourself in buzzing Streeterville three blocks from the Navy Pier, pop into Winter’s for classic jazz performances. You will find a ground-level stage in an intimate sleek and modern room referred to by Condé Nast Traveller as a “pocket of cool” with exposed brick-topped pillars holding up the ceiling.

The warm and cozy location takes its jazz seriously. Overlooking the Ogden Slip, the jazz spot offers great acoustics with decent views and cocktails. 

The venue is closed on Mondays and Tuesdays but offers 75-minute jazz sessions in the rest of the week, priding itself on hosting a ‘listening room’ where a policy of no talking is enforced. Each jazz show seats 100 in the listening room with an additional 25 in capacity at the bar and lounge area. VIP tickets give you the chance to be at eye level with musicians in front of the stage.

Expect to see acts such as the Chris White Quartet and Kimberly Gordon Quartet, as well as the Denise Thimes Quartet performing the music of Roberta Flack & Nina Simone.

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Best Clubs & Venues List

• The Green Mill – 4802 N Broadway, Chicago, IL 60640, United States
• Constellation – 3111 N Western Ave, Chicago, IL 60618, United States
• Jazz Showcase – 806 S Plymouth Ct, Chicago, IL 60605, United States
• Andy’s Jazz Club – 11 E Hubbard St, Chicago, IL 60611, United States
• Winter’s Jazz Club – 465 N McClurg Ct, Chicago, IL 60611, United States

As the current best jazz clubs in Chicago.

Discover next the best jazz clubs in New York, Copenhagen, Stockholm, Paris, and London.