By Bob Glaze
I love going to listen to live music in Chicago, but I now prefer to go to smaller venues rather than fight the crowds at the larger ones. My top recommendations include:
Located along the Ogden Slip in River East is Winter’s Jazz Club at 465 N. McClurg Ct. It is downstairs along the water. They have an excellent line-up of jazz performers from Wednesday to Sunday with two performances a night. There are tickets for general admission and for VIP seating which are reasonable. There is a one drink minimum per set per person. It is a small, intimate venue which features traditional jazz, swing, big band, New Orleans-style jazz and Gypsy-jazz. I asked Scott the owner where the name came from. He said Winter was his mother’s maiden name and that he got his love of jazz from her, so he named it in her honor!!! I highly recommend performances by Spider Saloff, The Paul Marinaro Quintet, Patricia Barber, Jo Ann Daugherty and Jane Monheit.
I have gone twice to a performance of Cole Porter music by Spider Saloff that were outstanding! I was back last month and enjoyed an evening with The Paul Marinaro Quintet performing the music of Nat King Cole.
The Green Mill, a former prohibition-era speakeasy, is now host to great jazz every night of the week. You will love the warm atmosphere. It is believed to be the oldest continuously run jazz club in the US. “The Mill’s Jazz Age pedigree has no equal in Chicago. Newspaper accounts of the era tell a lively tale of the locals’ proclivities and personalities. Jack “Machine Gun” McGurn, a Capone associate, supposedly owned part of the club during Prohibition, when tunnels under the bar were used to smuggle in booze, and kept a table reserved for his boss (walk into the bar, past the booths on the north wall, and it’s the first one you run into, positioned so you can see both entrances).” Superstars in the past routinely performed at the Mill, including Billie Holiday and Al Jolson.
Seating is first come, first served plus it is cash only. There is parking in the lot behind the club. 4802 N. Broadway.
Zebra Lounge: I enjoyed going back to this classic Chicago piano bar after many years. Located at 1220 N. State Pkwy, the bar features live piano players seven nights a week starting at 9pm. It is a fun spot with a zebra-themed design. I suggest going early to make sure you get a seat.
Celebrating its 85th Anniversary this year, the Zebra lounge has been in business in Chicago since 1929 and holds the third oldest liquor license in the city. The bar is located off the main Division strip inside the Canterbury Court apartment building. Known for secret celebrity drop-ins over the years, the bar is regularly packed with an eclectic mix of regulars and newcomers.
A fun spot to try is Buddy Guy’s Legends, a classic blues club at 700 S. Wabash. I went recently for the first time with a friend from Mexico who was in town on business. I wanted him to experience a true Chicago tradition. They offer music nightly from Wednesday through Sunday along with New Orleans-inspired food. I loved the atmosphere and the music!
The Club is the premier blues club located in Chicago. It is owned and operated by the Grammy winning blues legend himself, Buddy Guy.
Located in River North is Andy’s Jazz Club that features two live jazz bands nightly in a traditional setting. Opened as a neighborhood bar in 1951 by Andy Rizzuto, it became very popular with many in the newspaper business who worked nearby. He operated until 1975 when it was sold to the current ownership group that later added jazz to the mix. Make sure to add this to your list of things to do this winter. 11 E Hubbard St.
Thanks to a Prohibition Walking Tour I found The Drifter. It is in the basement of the Green Door Tavern and was the original speakeasy space from the 1920s. Today it is a dark, cozy space where you can have a great cocktail and see a fun show. The performers can be singers, Burlesque dancers, magicians or other acts. They open at 5pm and don’t take reservations, so go early to ensure you get a table. They are open Tuesday through Saturday. I highly recommend it. 676-8 N. Orleans.
Located in Ravenswood is Borelli’s Pizzeria at 2124 W. Lawrence Ave. Opened in 2023, this is a casual restaurant serving pizza and other Italian dishes. I went in July 2025 to have dinner with a friend and to hear a performance, by Opera Inter Alia, of French music to commemorate Bastille Day. This is a group of classically trained professional singers who perform there once a month. Borelli’s also hosts other weekly music events. I enjoyed my pappardelle pasta entree with beef and pork, the bruschetta and the cannoli for dessert. I recommend that you go to enjoy the experience.
Thalia Hall is located in Pilsen at 1807 S Allport St. in an historic landmark. It was founded by John Dusek at the turn of the century as a neighborhood establishment. Dusek was a family man, a tavern owner, and a facilitator of the arts.
They have three music venues Thalia Hall, the Tack Room and the Punch House with DJ’s. I have been in the past and enjoyed the experience. You can grab a bite before your concert upstairs at Mariscos San Pedro. It is excellent.
The Black-owned Bronzeville Winery is located on the first floor of a residential building at 4420 S. Cottage Grove Ave. Headed by Silver Room owner Eric Williams and managing partner Cecilia Cuff, this restaurant, wine bar and cultural space focuses on wine and comfort food such as lobster macaroni and cheese and shrimp and grits. The wine list is curated by Anika Ellison, “one of the few Black women sommeliers” per their website. It is an upscale restaurant with great art, service and food. I went for brunch on Sunday and enjoyed the shrimp and grits.
It also has a cultural space, patio and live music. It now hosts DJs from Wednesday through Saturday, as well as for Sunday brunch. They’re hosting more live music as well.
Located west of Lincoln Park near Elston, Ave is The Hideout, which is a fun local bar from 1934 located in a 100-year-old house. They offer music and entertainment throughout the week. 1354 W. Wabansia.
Hope you enjoy my recommendations. Let the music start!!!
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