West Loop

The West Loop packs an unusually wide range of live-music formats into a former meatpacking district whose industrial bones, exposed brick, and high ceilings now frame concert halls, piano bars, and performance restaurants alike. Bottom Lounge anchors the neighborhood's rock and indie calendar with a 700-capacity main hall and a separate 300-capacity Volcano Room. It books both underground and mainstream artists. City Winery doubles as a working winery and music room, pairing Mediterranean food and house-made wine with intimate sets covering soul, Americana, folk, blues, and jazz. Epiphany Center for the Arts operates out of a restored church and draws ticketed concert crowds. Alhambra Palace, a 24,000-square-foot Moorish-themed restaurant, features belly dancers and Middle Eastern singers on Friday and Saturday nights, with separate salsa and bachata dance socials also on the calendar. GG's Piano Bar runs live music Wednesday through Sunday, spotlighting local vocalists and cover acts on a baby grand piano. The Mine Music Hall keeps the night going until 4 AM Fridays and 5 AM Saturdays. The Wild Hare, Bandit, and Broken Hearts round out a street-level bar scene that adds reggae, indie rock, and late-night DJ sets to the mix.

Venues16

Upcoming shows200

Tomorrow · Wednesday, September 2 · 2 shows

Kimmi Bitter
8:00pm

Kimmi Bitter

Kimmi Bitter Dubbed "the future of classic country" by Saving Country Music, Kimmi Bitter is painting a whole new tapestry that drapes golden-era Countrypolitan with coastal desert twang. A rising force in the underground Americana scene she's mixing the old school with the new cool by capturing the

City Winery
7:30pm

Meagan McNeal & Keya Trammell: Make A Wish Benefit

,

Meagan McNeal & Keya Trammell: Make A Wish Benefit live on Wednesday, September 2nd at 7:30 PM! Join Pink Elephant Creatives for an unforgettable evening of soul, story, and purpose as Meagan McNeal and Keya Trammell take the stage at City Winery Chicago. Together, these two powerhouse Chicago vocalists will deliver a night of music, storytelling, and connection, celebrating the richness of Chicago’s creative community. A portion of the evening’s proceeds will benefit Make-A-Wish, helping grant life-changing wishes for children facing critical illnesses. Come for the music, leave knowing you helped make a meaningful impact.

from $36

Thursday, September 3 · 6 shows

Lyfe Jennings
7:30pm

Lyfe Jennings

City Winery Chicago Presents Lyfe Jennings live on Thursday, September 3rd at 7:30 PM! View all dates and times here! Not that he'd wish it on anyone, but it was during his ten-year sentence in prison that Lyfe Jennings developed his honest sound, thanks to isolation and Erykah Badu. It was an arson charge that put the Toledo, Ohio native in prison. His musical aspirations started in the church choir and grew up in the Dotsons, a teenage group that Lyfe formed with his brother and a couple cousins. Prison made his music deeper, according to Lyfe, and when a copy of Erykah Badu's Baduizm ended up in his cell in 1997, he was inspired and had the feeling that this introspective edge to his music was worth developing. Two days after his December 2002 release from prison, he recorded a four-song demo CD. The day after that, he was performing live in a club. He had only a month of freedom before he was on-stage at the famous Apollo. He was booed when he walked on-stage with an acoustic guitar, but when the Apollo audience heard his gritty falsetto and lyrical songwriting, they were swayed -- swayed to the tune of five amateur-night victories in a row. Lyfe figured he'd sold 1,000 copies of his four-song demo CD during his Apollo "residency." That, along with a ton of calls from promoters and record label execs on his answering machine back in Ohio, influenced Lyfeto move to New York City and pursue a major-label deal. Columbia had the right offer and released his debut, Lyfe 268-192 (his inmate number), in August 2004. A year after its original release, the album was reissued with a new version of "Hypothetically," featuring American Idol winner Fantasia added as a bonus track. The more hip-hop-oriented follow-up The Phoenix arrived in August 2006, with Three 6 Mafia and Young Buck making guest appearances. Lyfe Change -- released in April 2008 -- featured a handful of new production associates as well as a verse from T.I. Jennings. Lyfe moved to Warner Bros. and began working on another album, tentatively titled Sooner or Later, which he stated would be his last. It finally appeared in August 2010 as I Still Believe and featured guest spots from Bryan-Michael Cox, Warryn Campbell, Fabolous, Bobby Valentino, Ludacris, Anthony Hamilton, and Jazmine Sullivan. He did another prison stint for his actions in a 2008 domestic dispute and returned to music in October 2013 with Lucid, released on the Mass Appeal label. Like all of his previous studio releases, it peaked in the Top 10 of Billboard's R&B chart. Tree of Lyfe, recorded primarily in his home studio, followed as a Top 10 R&B hit.

from $66

Friday, September 4 · 11 shows

Diamondback
9:00pm

Diamondback

Diamondback has been a popular staple of the Chicago Music scene for decades. We bring our high energy sound to clubs, festivals and private events throughout the Midwest. Our extensive song list is truly a history of Country, and for that matter, American pop music, and promises something for every

Lyfe Jennings
6:00pm

Lyfe Jennings

City Winery Chicago Presents Lyfe Jennings live on Friday, September 4th at 6:00 PM! View all dates and times here! Not that he'd wish it on anyone, but it was during his ten-year sentence in prison that Lyfe Jennings developed his honest sound, thanks to isolation and Erykah Badu. It was an arson charge that put the Toledo, Ohio native in prison. His musical aspirations started in the church choir and grew up in the Dotsons, a teenage group that Lyfe formed with his brother and a couple cousins. Prison made his music deeper, according to Lyfe, and when a copy of Erykah Badu's Baduizm ended up in his cell in 1997, he was inspired and had the feeling that this introspective edge to his music was worth developing. Two days after his December 2002 release from prison, he recorded a four-song demo CD. The day after that, he was performing live in a club. He had only a month of freedom before he was on-stage at the famous Apollo. He was booed when he walked on-stage with an acoustic guitar, but when the Apollo audience heard his gritty falsetto and lyrical songwriting, they were swayed -- swayed to the tune of five amateur-night victories in a row. Lyfe figured he'd sold 1,000 copies of his four-song demo CD during his Apollo "residency." That, along with a ton of calls from promoters and record label execs on his answering machine back in Ohio, influenced Lyfeto move to New York City and pursue a major-label deal. Columbia had the right offer and released his debut, Lyfe 268-192 (his inmate number), in August 2004. A year after its original release, the album was reissued with a new version of "Hypothetically," featuring American Idol winner Fantasia added as a bonus track. The more hip-hop-oriented follow-up The Phoenix arrived in August 2006, with Three 6 Mafia and Young Buck making guest appearances. Lyfe Change -- released in April 2008 -- featured a handful of new production associates as well as a verse from T.I. Jennings. Lyfe moved to Warner Bros. and began working on another album, tentatively titled Sooner or Later, which he stated would be his last. It finally appeared in August 2010 as I Still Believe and featured guest spots from Bryan-Michael Cox, Warryn Campbell, Fabolous, Bobby Valentino, Ludacris, Anthony Hamilton, and Jazmine Sullivan. He did another prison stint for his actions in a 2008 domestic dispute and returned to music in October 2013 with Lucid, released on the Mass Appeal label. Like all of his previous studio releases, it peaked in the Top 10 of Billboard's R&B chart. Tree of Lyfe, recorded primarily in his home studio, followed as a Top 10 R&B hit.

from $66

Lyfe Jennings
9:30pm

Lyfe Jennings

City Winery Chicago Presents Lyfe Jennings live on Friday, September 4th at 9:30 PM! View all dates and times here! Not that he'd wish it on anyone, but it was during his ten-year sentence in prison that Lyfe Jennings developed his honest sound, thanks to isolation and Erykah Badu. It was an arson charge that put the Toledo, Ohio native in prison. His musical aspirations started in the church choir and grew up in the Dotsons, a teenage group that Lyfe formed with his brother and a couple cousins. Prison made his music deeper, according to Lyfe, and when a copy of Erykah Badu's Baduizm ended up in his cell in 1997, he was inspired and had the feeling that this introspective edge to his music was worth developing. Two days after his December 2002 release from prison, he recorded a four-song demo CD. The day after that, he was performing live in a club. He had only a month of freedom before he was on-stage at the famous Apollo. He was booed when he walked on-stage with an acoustic guitar, but when the Apollo audience heard his gritty falsetto and lyrical songwriting, they were swayed -- swayed to the tune of five amateur-night victories in a row. Lyfe figured he'd sold 1,000 copies of his four-song demo CD during his Apollo "residency." That, along with a ton of calls from promoters and record label execs on his answering machine back in Ohio, influenced Lyfeto move to New York City and pursue a major-label deal. Columbia had the right offer and released his debut, Lyfe 268-192 (his inmate number), in August 2004. A year after its original release, the album was reissued with a new version of "Hypothetically," featuring American Idol winner Fantasia added as a bonus track. The more hip-hop-oriented follow-up The Phoenix arrived in August 2006, with Three 6 Mafia and Young Buck making guest appearances. Lyfe Change -- released in April 2008 -- featured a handful of new production associates as well as a verse from T.I. Jennings. Lyfe moved to Warner Bros. and began working on another album, tentatively titled Sooner or Later, which he stated would be his last. It finally appeared in August 2010 as I Still Believe and featured guest spots from Bryan-Michael Cox, Warryn Campbell, Fabolous, Bobby Valentino, Ludacris, Anthony Hamilton, and Jazmine Sullivan. He did another prison stint for his actions in a 2008 domestic dispute and returned to music in October 2013 with Lucid, released on the Mass Appeal label. Like all of his previous studio releases, it peaked in the Top 10 of Billboard's R&B chart. Tree of Lyfe, recorded primarily in his home studio, followed as a Top 10 R&B hit.

from $66

The Wild Hare
8:00pm

Green Light Fridays

Join us for round two of Green Light Fridays at Wild Hare, hosted by Kjdoubletrey! You'll be in the mix with two heavy hitters: DJ Dez and DJ Devo all night. Music from hip hop to RnB to throwbacks will be played! Buy Tickets X More Information

Saturday, September 5 · 6 shows

City Winery
12:00pm

Gospel Melodies Day Party & Brunch

City Winery Chicago Presents Gospel Melodies Day Party & Brunch: A Celebration of Faith, Fellowship & Culture live on Saturday, September 5th at 12:00 PM! A unique experience blending the best of gospel music, culture, and community all wrapped in the energy of a live day party! Featuring Dj Ty King, The GM Band, and Special Guest Artists, we fuse Gospel with R&B vibes, Holy Hip-Hop, Rhythm & Praise, and more — creating a powerful sound that moves both soul and spirit. This is an interactive celebration of faith, unity, and joy — where people from all walks of life come together to sing, dance, testify, and worship in an uplifting, unforgettable atmosphere. This isn’t your traditional church event — it’s a “bridging the gap” experience built for everyone! Founded & Curated By Dr. Nathaniel “FloWay” Felton. Hosted By Charles Clark. Get ready to celebrate t

from $36

The Wild Hare
8:00pm

PYRO: Carribean Heat

Caribbean Heat celebrates the sounds that have moved dance floors across Jamaica, Trinidad & Tobago, Haiti, Dominica, St. Lucia and beyond. Expect five hours of dancehall, reggae, soca, kompa, bouyon, dennery segment, dub, island classics and more throughout the night. Buy Tickets X More Information

Sunday, September 6 · 5 shows

The Westerlees
7:00pm

The Westerlees

The Westerlees swing band plays both rare and popular tunes from the 1920s, 1930s, and 1940s.Everything from the Light Crust Doughboys to Bob Wills to Hank Williams is performed with levity and humor. Swing-era standards are carefully selected and arranged for maximum danceabilty. They also have man

Christopher Williams
5:00pm

Christopher Williams

City Winery Chicago Presents Christopher Williams live on Sunday, September 6th at 5:00 PM! View all dates / times here! Christopher Williams comes to Chicago for a special two show Sunday engagement, giving fans double the opportunity to experience his signature blend of R&B and New Jack Swing. With decades of success as a recording artist and actor, Williams continues to captivate audiences with his smooth delivery and undeniable stage presence. From “Dreamin’” to his work on stage and screen, his artistry remains as compelling as ever. Join us for an intimate performance that pairs timeless music with exceptional food and wine. Choose your show and reserve your seats early for this limited engagement.

from $54

Monday, September 7 · 4 shows

Musiq Soulchild
6:00pm

Musiq Soulchild

City Winery Chicago Presents Musiq Soulchild live on Monday, September 7th at 6:00 PM! View all shows with Musiq Soulchild here! Musiq Soulchild, born Taalib Johnson, is one of the most influential R&B singers of his generation. Weaned on Marvin Gaye, Stevie Wonder, and Donny Hathaway, Musiq pioneered the "neo-soul" movement of the early millennium. He has received 13 Grammy nominations and has sold millions of records world-wide. He is still one of the most popular performers of his time and a true artist. Known for his raw vocal talent, Musiq went from signing on the street corners of Philadelphia in the late g0's, to landing a big record deal with Def Jam in 2000; ushering in a new age sound of his own. He has received awards from Billboard, BET, ASCAP, BMI, and Soul Train. He has also earned award nominations from MTV. the American Music Awards and the NAACP.

from $90

Musiq Soulchild
9:30pm

Musiq Soulchild

City Winery Chicago Presents Musiq Soulchild live on Monday, September 7th at 9:30 PM! View all shows with Musiq Soulchild here! Musiq Soulchild, born Taalib Johnson, is one of the most influential R&B singers of his generation. Weaned on Marvin Gaye, Stevie Wonder, and Donny Hathaway, Musiq pioneered the "neo-soul" movement of the early millennium. He has received 13 Grammy nominations and has sold millions of records world-wide. He is still one of the most popular performers of his time and a true artist. Known for his raw vocal talent, Musiq went from signing on the street corners of Philadelphia in the late g0's, to landing a big record deal with Def Jam in 2000; ushering in a new age sound of his own. He has received awards from Billboard, BET, ASCAP, BMI, and Soul Train. He has also earned award nominations from MTV. the American Music Awards and the NAACP.

from $90

Tuesday, September 8 · 1 show

Wednesday, September 9 · 2 shows

Broken Hearts
8:00pm

Rami Gabriel & Alex Hall

Rami Gabriel is a composer and producer who plays Oud, Buzuq, and Guitar. Rami leads Chicago favorites The Arab Blues and Rami & the Reliables. His solo album, That's what I been sayin' was released by Sooper records in 2024. Alex Hall is a drummer and the recording engineer who runs Reliable Record

Thursday, September 10 · 4 shows

Friday, September 11 · 5 shows

Saturday, September 12 · 10 shows

James Gedda & The Big Breakfast
9:00pm

James Gedda & the Big Breakfast

James Gedda is an up-and-coming Country and Americana singer-songwriter with a booming voice and a plainspoken honesty in his lyrics. The Crown Point, IN native has drawn comparisons to the likes of Johnny Cash and Merle Haggard with his earthy baritone, and he regularly covers such classics, but wh

Sunday, September 13 · 5 shows

Broken Hearts
10:00pm

John Ballantyne's Crazy Heart

John BallantyneMore often than not, the road to country music stardom originates in Texas, Tennessee, or another time-honored Southern destination. John Ballantyne’s story arc reads way differently. Fast becoming recognized as one of Chicago’s premier country singers and songwriters, Ballantyne was

Tuesday, September 15 · 1 show

Wednesday, September 16 · 2 shows

Broken Hearts
8:00pm

Pistol Pete

From the first note to the last, Pistol Pete will take you on a high energy musical journey. You will want to get out on the dance floor or play "air guitar" right along with him. The consummate professional, Pete tunes up his guitar and then tunes into his audience. Whether he is playing for a smal

Thursday, September 17 · 3 shows

Friday, September 18 · 8 shows

Broken Hearts
9:00pm

The Rangers · Alma Russ (nc)

Homegrown Chicagoland Country and Wild Western. The Rangers, full steam ahead on their “Cowboy in a Bottle Tour” bring an electric and dynamic show to the stage, and make every show a night to remember! The Rangers Band (Facebook) @therangersband (instagram) @therangersband (TikTok)

The Wild Hare
8:00pm

NOCTÉ ROYALE Presents: Midnight society

Music by DJ Mile High & DJ Bigg Baby! Get ready for an unforgettable night filled with upscale vibes, premium bottle service, cocktails and the city’s best Reggaeton, Afro Beats, Hip-Hop, Juke, and R&B all under one roof. Buy Tickets X More Information

Saturday, September 19 · 7 shows

Broken Hearts
9:00pm

Joe Wortell · Doc Brown Band

Country music has always been about the voice and the story. Well, Joe Wortell sure has the voice and he sure as hell has some stories. Hailing from the City of Chicago where he works at his family's metal fabrication factory Joe cut his teeth in the bars and Honky Tonks playing the hell out of his

Sunday, September 20 · 3 shows

Tuesday, September 22 · 2 shows

Wednesday, September 23 · 3 shows

Broken Hearts
7:00pm

Windy City Cowboy Club

Claire Chm is a line dance instructor and a member of the Line Dancers of Chicago community. She and her friends are excited to bring line dancing back to Broken Hearts! Whether you have two left feet or you’re a line dancing pro, we’ve got lessons and song selections that will keep you on the dance

Thursday, September 24 · 3 shows

Friday, September 25 · 3 shows

Saturday, September 26 · 7 shows

The Wild Hare
8:00pm

Dj E-magic: poetic justus

Don’t miss out on Poetic JustUs, the home of the Sing Along Party and open mic poetry. Not the traditional R&B songs you hear often. We are playing those cuts you forgot about. Buy Tickets X More Information

Sunday, September 27 · 5 shows

Monday, September 28 · 1 show

Tuesday, September 29 · 2 shows

Wednesday, September 30 · 4 shows

Thursday, October 1 · 2 shows

Friday, October 2 · 4 shows

Saturday, October 3 · 3 shows

Sunday, October 4 · 3 shows

Tuesday, October 6 · 1 show

Wednesday, October 7 · 1 show

Thursday, October 8 · 2 shows

Friday, October 9 · 3 shows

Saturday, October 10 · 3 shows

Sunday, October 11 · 2 shows

Wednesday, October 14 · 1 show

Thursday, October 15 · 1 show

Friday, October 16 · 4 shows

Saturday, October 17 · 4 shows

Sunday, October 18 · 3 shows

Monday, October 19 · 1 show

Tuesday, October 20 · 1 show

Wednesday, October 21 · 2 shows

Thursday, October 22 · 2 shows

Friday, October 23 · 4 shows

Saturday, October 24 · 3 shows

Sunday, October 25 · 2 shows

Tuesday, October 27 · 1 show

Friday, October 30 · 1 show

Saturday, October 31 · 2 shows

Sunday, November 1 · 1 show

Wednesday, November 4 · 3 shows

Thursday, November 5 · 2 shows

Friday, November 6 · 4 shows

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