City Winery
1200 W Randolph St
City Winery is a West Loop venue combining live music and comedy with an on-site winery, restaurant, and wine bar. The space books R&B, soul, rock, blues, and jazz acts alongside comedy shows, and pairs performances with Mediterranean-inspired dining and house-made wines. Brunch, wine tastings, and chef dinners round out the programming.
Hours:
- Mon–Tue 4pm–9pm
- Wed–Thu 4pm–10pm
- Fri 2pm–11pm
- Sat 10am–11pm
- Sun 10am–9pm
Upcoming shows50 listings
Tue, Oct 20
Fri, Oct 23
Sat, Oct 24
Sun, Oct 25
- S12:00pmSoul Brunch: Ladies of the 80sCity Winery Chicago & PureSoul Presents Soul Brunch: Ladies of the 80s live on Sunday, October 25th at 12:00 PM! It's time for electric grooves with Soul Brunch: Ladies of the 80s, presented by PureSoul. This high-energy event blends delicious brunch classics and bottomless vibes with a live, soulful tribute to the legendary women who ruled the 1980s music scene — from Whitney Houston and Chaka Khan to Anita Baker and Janet Jackson. In the hands of the PureSoul, you'll be celebrating nostalgic hits, great food, and timeless star power. Enjoy a full brunch buffet for $25 (separate price from show).R&Bfrom $30
- Z7:00pmZoso: The Ultimate Led Zeppelin ExperienceCity Winery Chicago Presents Zoso: The Ultimate Led Zeppelin Experience live on Sunday, October 25th at 7:00 PM! Celebrating 31 years of touring in 2026, Zoso has become one of the most iconic and respected Led Zeppelin tribute experiences in the world, having played over 4,900 shows in all 50 states and internationally. Known for their unparalleled dedication to faithfully recreating the legendary band's live performances, Zoso has earned accolades from both critics and fans alike. Zoso’s live performances focus on the raw energy and intricate musicality of Led Zeppelin’s best-known hits and deeper tracks, with a particular emphasis on recreating their live show experience. The band’s commitment to authenticity has earned them praise from major outlets, with the LA Times calling them “head and shoulders above all other Led Zeppelin tributes,” and the St. Petersburg Times describing them as “the most exacting of all the Led Zeppelin tributes.”Classic rockfrom $36
Tue, Oct 27
Wed, Oct 28
Thu, Oct 29
Sun, Nov 1
5:00pmVivian GreenCity Winery Chicago Presents Vivian Green live on Sunday, November 1st at 7:00 PM! Born in Philadelphia Vivian Green was raised in a home where Motown classics were always blaring. Her parents were avid music lovers with talents of their own. Her mother sang and her father, an engineer, played the trumpet. She began singing at age five, started playing piano by eight, and by eleven began writing songs. She knew by age thirteen, that she wanted to sing professionally. She honed her craft at the piano everyday after school, writing mature love songs far beyond her years. At fifteen she began to record at multi-platinum group Boyz II Men’s studio. This gave Green a taste of life as an artist and led to an opportunity to write with the band. At seventeen she received her first professional songwriting credit co-writing the song “Dear God” on their platinum selling album Evolution. Green was also offered a recording contract from Ruffhouse Columbia, but her protective parents felt she wasn’t ready. Determined to be a recording artist, Green continued to record relentlessly. Her mature, sultry voice and knowledge of material allowed her to sing in some of Philadelphia’s premiere jazz clubs despite her age. She also obtained a job singing with two of the top party orchestras in Philadelphia. Additionally, Green sang background for renown soul singer/actress Jill Scott. Green teamed up with Grammy nominated singer/songwriter Eric Roberson to create the demo that would win her a deal with Sony Music. The demo contained her first smash hit “Emotional Roller coaster”. Her debut album A Love Story released in 2002 and was certified Gold. It received rave reviews from People, Billboard, Rolling Stone, and USA Today to name a few. Her second album Vivian released in 2005 and produced “Gotta Go Gotta Leave” a no.1 AC/Dance hit. The New York Times called the album a “stellar sophomore performance”. Vivian has several notable features and collaborations. She made her film debut in the Oscar nominated biopic De Lovely portraying a jazz singer performing the classic “Love For Sale”. She also appeared in the TV Series American Dreams, portraying Brenda Hollaway singing “Every Little Bit Hurts”. Green wrote the songs for playwright/film-maker David. E. Talbert’s stage play Love in the Nick of Thyme. She is featured on Cyndi Lauper’s album The Body Acoustic and the late Guru’s Jazzmatazz 4. She was also featured on Soundtrack to a Revolution, a compilation of spiritual songs featuring artist like Anthony Hamilton, John Legend, The Roots, and Mary Mary. Most recently she collaborated with jazz pianist Brian Culbertson for his album Dreams and produced the top 10 AC hit “Still Here”. The song also appeared on Vivian’s 4th album The Green Room. In 2004 she gave birth to her son Jordan who was born with an undiagnosed syndrome. Between 2005 and 2010, Jordan’s multiple surgeries and health issues demanded her to take a hiatus from releasing albums, but her strength and resilience always pushed her to continue doing what she loves. “Being Jordan’s mom is my life and I wouldn’t have it any other way”, says Green. Green is an advocate for children with special needs and will push her #IamDifferentIamHuman PSA campaign with the release of Vivid. “It’s something I’ve been pregnant with for quite some time” says Green. In the ever-changing music business Green has stayed afloat delivering classy, heartfelt, and often therapeutic music for her fans. Vivid will assuredly continue her legacy in music.” Some fans want me to deliver brokenhearted music, and perhaps I will in the future if I’m in that space”, says Green. “What I can and will always do is produce music that is from my heart. I think that’s the essence of soul music anyway. Vivid definitely won’t be getting you down. If anything, it’ll make you get up”.R&B · JazzSet 1from $66
8:30pmVivian GreenCity Winery Chicago Presents Vivian Green live on Sunday, November 1st at 7:00 PM! Born in Philadelphia Vivian Green was raised in a home where Motown classics were always blaring. Her parents were avid music lovers with talents of their own. Her mother sang and her father, an engineer, played the trumpet. She began singing at age five, started playing piano by eight, and by eleven began writing songs. She knew by age thirteen, that she wanted to sing professionally. She honed her craft at the piano everyday after school, writing mature love songs far beyond her years. At fifteen she began to record at multi-platinum group Boyz II Men’s studio. This gave Green a taste of life as an artist and led to an opportunity to write with the band. At seventeen she received her first professional songwriting credit co-writing the song “Dear God” on their platinum selling album Evolution. Green was also offered a recording contract from Ruffhouse Columbia, but her protective parents felt she wasn’t ready. Determined to be a recording artist, Green continued to record relentlessly. Her mature, sultry voice and knowledge of material allowed her to sing in some of Philadelphia’s premiere jazz clubs despite her age. She also obtained a job singing with two of the top party orchestras in Philadelphia. Additionally, Green sang background for renown soul singer/actress Jill Scott. Green teamed up with Grammy nominated singer/songwriter Eric Roberson to create the demo that would win her a deal with Sony Music. The demo contained her first smash hit “Emotional Roller coaster”. Her debut album A Love Story released in 2002 and was certified Gold. It received rave reviews from People, Billboard, Rolling Stone, and USA Today to name a few. Her second album Vivian released in 2005 and produced “Gotta Go Gotta Leave” a no.1 AC/Dance hit. The New York Times called the album a “stellar sophomore performance”. Vivian has several notable features and collaborations. She made her film debut in the Oscar nominated biopic De Lovely portraying a jazz singer performing the classic “Love For Sale”. She also appeared in the TV Series American Dreams, portraying Brenda Hollaway singing “Every Little Bit Hurts”. Green wrote the songs for playwright/film-maker David. E. Talbert’s stage play Love in the Nick of Thyme. She is featured on Cyndi Lauper’s album The Body Acoustic and the late Guru’s Jazzmatazz 4. She was also featured on Soundtrack to a Revolution, a compilation of spiritual songs featuring artist like Anthony Hamilton, John Legend, The Roots, and Mary Mary. Most recently she collaborated with jazz pianist Brian Culbertson for his album Dreams and produced the top 10 AC hit “Still Here”. The song also appeared on Vivian’s 4th album The Green Room. In 2004 she gave birth to her son Jordan who was born with an undiagnosed syndrome. Between 2005 and 2010, Jordan’s multiple surgeries and health issues demanded her to take a hiatus from releasing albums, but her strength and resilience always pushed her to continue doing what she loves. “Being Jordan’s mom is my life and I wouldn’t have it any other way”, says Green. Green is an advocate for children with special needs and will push her #IamDifferentIamHuman PSA campaign with the release of Vivid. “It’s something I’ve been pregnant with for quite some time” says Green. In the ever-changing music business Green has stayed afloat delivering classy, heartfelt, and often therapeutic music for her fans. Vivid will assuredly continue her legacy in music.” Some fans want me to deliver brokenhearted music, and perhaps I will in the future if I’m in that space”, says Green. “What I can and will always do is produce music that is from my heart. I think that’s the essence of soul music anyway. Vivid definitely won’t be getting you down. If anything, it’ll make you get up”.R&B · JazzSet 2from $66
Mon, Nov 2
Tue, Nov 3
Wed, Nov 4
Thu, Nov 5
Sat, Nov 7
- S12:00pmSoul Brunch — A Tribute to Al Green & Bobby WomackCity Winery Chicago & PureSoul Presents Soul Brunch — A Tribute to Al Green & Bobby Womack on Saturday, November 7th at 12:00 PM!R&Bfrom $30
7:30pmJoshua Radin with Raye ZaragozaCity Winery Chicago Presents Joshua Radin with Raye Zaragoza live on Saturday, November 7th at 7:30 PM! View all dates/times here! Since emerging in 2004, Radin has become one of the most beloved voices in modern singer songwriter music, amassing more than one billion streams worldwide and selling over a million albums. His gold certified hit “I’d Rather Be With You” helped introduce his gentle, emotionally rich style to a wide audience, while his songs have appeared in more than 200 films, television series, and commercials. Radin has also delivered memorable performances on major stages and television programs including The Ellen DeGeneres Show, The Today Show, The Tonight Show, Jimmy Kimmel LIVE! and Conan. With a catalog spanning ten albums, Radin continues to evolve as an artist. His latest project, One Day Home, explores love, reflection, and personal growth through both lush studio recordings and intimate piano vocal performances. Join us for a special Saturday night of beautifully crafted songs and heartfelt storytelling. Reserve your seats now for an unforgettable evening of live music.Folk rock · Singer-songwriterfrom $54
Sun, Nov 8
- D12:00pmDJ Sean Mac + Joe Global: Scorpio Season R&B Singalong BrunchCity Winery Chicago Presents DJ Sean Mac + Joe Global: Libra Season R&B Singalong Brunch live on Tuesday, September 15th at 7:30 PM! JOE GLOBAL& SEAN MAC The R&B Sing Along is an exciting and submersive experience, a journey through the greatest genre of music, R&B. Nationally celebrated and local favorite DJs, Joe Global & Sean Mac brings an explosive collaboration of entertainment, comedy and crowd interactions while the audience sing along to their favorite songs at the top of their lungs. The R&B Sing Along has sold out shows across the country. Attracting R&B lovers from all age groups and demographics. Everybody singing along to songs with their plastic microphones with friends. No one is left out. Joe Global & Sean Mac test the knowledge of the audience of musical mastery. Playing R&B songs from the current hits, to the 90s, 80s, 70s and even the 60s. For fun they even play some of the theme songs from our favorite sitcoms. It's so much nostalgic fun. The R&B Sing Along performance was featured on The R&B Experience National Tour starring Bell Biv Devoe, Tyrese, Tank & Ginuwine & Tevin Campbell. Also at the United Center for a sold out concert featuring Tink and other artists, and recently headlined at the Englewood Music Fest with 40,000 attendees.R&Bfrom $42
7:00pmJoshua Radin with Raye ZaragozaCity Winery Chicago Presents Joshua Radin with Raye Zaragoza live on Sunday, November 8th at 7:00 PM! View all dates/times here! Since emerging in 2004, Radin has become one of the most beloved voices in modern singer songwriter music, amassing more than one billion streams worldwide and selling over a million albums. His gold certified hit “I’d Rather Be With You” helped introduce his gentle, emotionally rich style to a wide audience, while his songs have appeared in more than 200 films, television series, and commercials. Radin has also delivered memorable performances on major stages and television programs including The Ellen DeGeneres Show, The Today Show, The Tonight Show, Jimmy Kimmel LIVE! and Conan. With a catalog spanning ten albums, Radin continues to evolve as an artist. His latest project, One Day Home, explores love, reflection, and personal growth through both lush studio recordings and intimate piano vocal performances. Join us for a special Saturday night of beautifully crafted songs and heartfelt storytelling. Reserve your seats now for an unforgettable evening of live music.Folk rock · Singer-songwriterfrom $54
Mon, Nov 9
Tue, Nov 10
Thu, Nov 12
Fri, Nov 13
- A6:00pmAmi Taf Ra & Kamasi Washington presenting The Prophet & The MadmanCity Winery Chicago Presents Ami Taf Ra & Kamasi Washington presenting The Profit & The Madman live on Friday, November 13th at 6:00 PM! View all dates / times hereR&B · BluesSet 1from $60
- A9:30pmAmi Taf Ra & Kamasi Washington presenting The Prophet & The MadmanCity Winery Chicago Presents Ami Taf Ra & Kamasi Washington presenting The Profit & The Madman live on Friday, November 13th at 9:30 PM! View all dates / times hereR&B · BluesSet 2from $60
Sat, Nov 14
- A6:00pmAmi Taf Ra & Kamasi Washington presenting The Prophet & The MadmanCity Winery Chicago Presents Ami Taf Ra & Kamasi Washington presenting The Profit & The Madman live on Saturday, November 14th at 6:00 PM! View all dates / times hereR&B · BluesSet 1from $60
- A9:30pmAmi Taf Ra & Kamasi Washington presenting The Prophet & The MadmanCity Winery Chicago Presents KAmi Taf Ra & Kamasi Washington presenting The Profit & The Madman live on Saturday, November 14th at 9:30 PM! View all dates / times hereR&B · BluesSet 2from $60
Sun, Nov 15
- S12:00pmSoul Brunch: A Tribute to Rick & TeenaCity Winery Chicago & PureSoul Presents Soul Brunch: A Tribute to Rick & Teena on Sunday, November 15th at 12:00 PM! Get ready for a high-energy afternoon as PureSoul Chicago dives into the electrifying worlds of Teena Marie and Rick James, two artists who blurred the lines between funk, soul, and rock with fearless style. From Teena’s unforgettable solo hits like Square Biz and Lovergirl to Rick’s funk-driven anthems like Super Freak and Give It to Me Baby—plus their iconic duet Fire and Desire—this tribute brings their bold, unapologetic sound to life with raw passion and groove.R&Bfrom $30
7:00pmMarcus Veltri & Rob Landes - Requests on the RoadCity Winery Chicago Presents Marcus Veltri & Rob Landes - Requests on the Road live on Sunday, November 15th at 7:00 PM! Viral video sensations Marcus Veltri and Rob Landes have built a global audience by taking song requests from strangers and turning them into unforgettable musical moments. Together, their videos have generated more than one billion views across social media. Now, the piano and violin duo is bringing that experience to the stage. Audiences will hear their most popular covers, witness their signature improvisational style, and have the chance to shape the show through live song requests. Rob Landes began playing violin at age three and is known for surprising strangers with music in unexpected ways. Marcus Veltri taught himself piano at age fifteen and quickly became passionate about performing his favorite songs and creating new arrangements. Part concert and part interactive experience, every show is unique. With no opening act, the evening is centered entirely around the music, the audience, and the spontaneous moments that have made Marcus and Rob one of the internet's most recognizable musical duos.Pop · Rockfrom $36
Mon, Nov 16
Tue, Nov 17
Wed, Nov 18
Thu, Nov 19
Fri, Nov 20
Sat, Nov 21
Sun, Nov 22
Tue, Nov 24
Wed, Nov 25
Fri, Nov 27
Sat, Nov 28
Sun, Nov 29
Wed, Dec 2
Sat, Dec 5
6:00pmJubu Smith Presents A Tribute to Frankie Beverly Featuring DeronCity Winery Chicago Presents Jubu Smith Presents A Tribute to Frankie Beverly Featuring Deron live on Saturday, December 5th at 6:00 PM! View all dates times here Smith spent a decade with the Tonies before going on the road for a year and a half with Whitney Houston. For the past 15 years, he’s been touring internationally eight months per year, primarily on weekends, with Maze, featuring Frankie Beverly. Those credits don’t include countless recording sessions with the likes of Luther Vandross, Mary J. Blige, Boyz II Men, Toni Braxton, George Duke and George Benson.R&B · JazzSet 1from $45.6
9:30pmJubu Smith Presents A Tribute to Frankie Beverly Featuring DeronCity Winery Chicago Presents Jubu Smith Presents A Tribute to Frankie Beverly Featuring Deron live on Saturday, December 5th at 9:30 PM! View all dates times here Smith spent a decade with the Tonies before going on the road for a year and a half with Whitney Houston. For the past 15 years, he’s been touring internationally eight months per year, primarily on weekends, with Maze, featuring Frankie Beverly. Those credits don’t include countless recording sessions with the likes of Luther Vandross, Mary J. Blige, Boyz II Men, Toni Braxton, George Duke and George Benson.R&B · JazzSet 2from $45.6
Sun, Dec 6
5:00pmKurt Elling Sings ChristmasCity Winery Chicago Presents Kurt Elling Sings Christmas - The Beautiful Day live on Sunday, December 6th at 5:00 PM! View all dates / times here Two-time GRAMMY Award winner and 17-time nominee Kurt Elling has secured his place among the world’s foremost jazz vocalists, renowned for his singular combination of robust swing, extraordinary musicianship and poetic insight. Declared “the standout male vocalist of our time” by The New York Times, Elling’s career has been marked by decades of critical acclaim and an unprecedented fourteen-year run atop the DownBeat Critics Poll. Most recently, Elling brought his unmistakable voice and commanding stage presence to Broadway, making his Broadway debut as Hermes in the Tony Award-winning musical Hadestown. For the holiday season, Elling returns to the music of The Beautiful Day: Kurt Elling Sings Christmas, his distinctive and deeply personal celebration of Christmas. Inventive, warm and full of surprises, The Beautiful Day reimagines the sounds of the season, combining traditional carols in fresh arrangements with unexpected songs and rediscovered treasures. At its heart are the universal themes of hope, light, wonder, mystery and goodwill that have always defined Elling’s approach to the holidays. “I knew I didn’t want to make a ‘religious’ record, just as I knew I didn’t want to make a standard, swingin’ jazzy Christmas,” Elling has said. “I’m trying to expand my consciousness and embrace the goodness of the season, and I want to include everybody. For me, Christmas is a time of consideration, of pondering mysteries.” Bringing that spirit to the stage, Kurt Elling’s holiday concerts offer an evening that is at once joyful, searching, soulful and unmistakably his own — a contemporary celebration of the season from one of today’s most acclaimed and adventurous vocal artists.Vocal jazz · BluesSet 1from $57.6
8:30pmKurt Elling Sings ChristmasCity Winery Chicago Presents Kurt Elling Sings Christmas - The Beautiful Day live on Sunday, December 6th at 5:00 PM! View all dates / times here Two-time GRAMMY Award winner and 17-time nominee Kurt Elling has secured his place among the world’s foremost jazz vocalists, renowned for his singular combination of robust swing, extraordinary musicianship and poetic insight. Declared “the standout male vocalist of our time” by The New York Times, Elling’s career has been marked by decades of critical acclaim and an unprecedented fourteen-year run atop the DownBeat Critics Poll. Most recently, Elling brought his unmistakable voice and commanding stage presence to Broadway, making his Broadway debut as Hermes in the Tony Award-winning musical Hadestown. For the holiday season, Elling returns to the music of The Beautiful Day: Kurt Elling Sings Christmas, his distinctive and deeply personal celebration of Christmas. Inventive, warm and full of surprises, The Beautiful Day reimagines the sounds of the season, combining traditional carols in fresh arrangements with unexpected songs and rediscovered treasures. At its heart are the universal themes of hope, light, wonder, mystery and goodwill that have always defined Elling’s approach to the holidays. “I knew I didn’t want to make a ‘religious’ record, just as I knew I didn’t want to make a standard, swingin’ jazzy Christmas,” Elling has said. “I’m trying to expand my consciousness and embrace the goodness of the season, and I want to include everybody. For me, Christmas is a time of consideration, of pondering mysteries.” Bringing that spirit to the stage, Kurt Elling’s holiday concerts offer an evening that is at once joyful, searching, soulful and unmistakably his own — a contemporary celebration of the season from one of today’s most acclaimed and adventurous vocal artists.Vocal jazz · BluesSet 2from $57.6
Mon, Dec 7
Tue, Dec 8
Sun, Dec 13
- D5:00pmDamien Escobar - Art of a Gentleman TourCity Winery Chicago Presents Damien Escobar live on Sunday, December 13th at 5:00 PM! View all dates / times here Experience the power of the violin like never before when two-time Emmy Award-winning artist Damien Escobar brings two shows to City Winery Chicago on December 13. Known as the “King of Strings,” Escobar has spent nearly two decades breaking barriers and redefining what contemporary violin can sound like. The Jamaica, Queens native went from performing for commuters in New York City subways to playing for audiences around the world, serenading everyone from Oprah to the Obamas along the way. With more than one million records sold, Billboard chart success, an NAACP Award nomination, and his #1 song “Taboo,” Escobar has built a career around proving the extraordinary power of instrumental music. His album Gemini continues that mission, blending undeniable musicianship with the passion, charisma, and emotion that have become signatures of his performances. See Damien Escobar up close at City Winery Chicago for an intimate evening of electrifying musicianship, dinner, wine, and the unmistakable sound of the King of Strings.R&BSet 1from $72
- D8:30pmDamien Escobar - Art of a Gentleman TourCity Winery Chicago Presents Damien Escobar live on Sunday, December 13th at 8:30 PM! View all dates / times here Experience the power of the violin like never before when two-time Emmy Award-winning artist Damien Escobar brings two shows to City Winery Chicago on December 13. Known as the “King of Strings,” Escobar has spent nearly two decades breaking barriers and redefining what contemporary violin can sound like. The Jamaica, Queens native went from performing for commuters in New York City subways to playing for audiences around the world, serenading everyone from Oprah to the Obamas along the way. With more than one million records sold, Billboard chart success, an NAACP Award nomination, and his #1 song “Taboo,” Escobar has built a career around proving the extraordinary power of instrumental music. His album Gemini continues that mission, blending undeniable musicianship with the passion, charisma, and emotion that have become signatures of his performances. See Damien Escobar up close at City Winery Chicago for an intimate evening of electrifying musicianship, dinner, wine, and the unmistakable sound of the King of Strings.R&BSet 2from $72