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Live music in Chicago this week, Sun, Sep 27 – Sat, Oct 3. 500+ shows across Chicagoland and NW Indiana.

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Today · Sun, Sep 27 · 142 shows

Broken HeartsWest Loop
Broken Hearts
9:00pm

Too Gold · Garry Princeton & the Flyover Country

Rock · Country

TOO GOLD plays fuzzed-out country rock in backyards, basements, and dive bars around Chicago. Tom Hays and Margaret Stephenson started singing and writing songs together after meeting on a group trip to a cabin deep in the Wisconsin Northwoods. They’re joined by longtime friends Devin Byrd on bass a

City WineryWest Loop
City Winery
12:00pm

The Boy Band Project Brunch

Join us for this month's Chef & Winemaker Dinner: Gather & Give Thanks, a four-course dining experience inspired by gratitude, seasonal abundance, and the comforting flavors of late fall.

City WineryWest Loop
City Winery
7:00pm

Mama Dea's Juke Box: A Musical Tribute to Tyler Perry

City Winery Chicago & Jai Brenai Productions Presents Mama Dea's Juke Box: A Musical Tribute to Tyler Perry live on Sunday, September 27th at 7:00 PM! From the producer of Jai Brenai Productions comes an unforgettable theatrical concert experience inspired by the beloved characters, unforgettable moments, and timeless storytelling that audiences have loved for years. Join Mama Dea, The Faithful Daughter, The Hustler Uncle, The Funny Neighbor, The Firecracker Auntie, and The Church Ladies snd more… as they take audiences on an emotional and hilarious musical journey through faith, family, forgiveness, and second chances.

from $36

Martyrs'North Center
ifwewait.
8:00pm

ifwewait. - Album Release!

, ,

Album release show. Woonds is a fresh on the scene Chicago outfit with influences ranging from hard metallic sound to soft melodic presence.

Doors 7:30pm

$10adv/$15doors

ReggiesSouth Loop
Vader
7:00pmRock Club

Vader

with , ,

Black metal · Death metal

Doors 6:00pm

Tomorrow · Mon, Sep 28 · 48 shows

City WineryWest Loop
City Winery
7:30pm

A Tribute To A Tribe Called Quest: Presented by The J. Grant Experience

Hip-hop

City Winery Chicago Presents A Tribute To A Tribe Called Quest: Presented by The J. Grant Experience Featuring: Marqueal Jordan, Mz. Keeta, & D2G live on Monday, September 28th at 7:30 PM! What began on May 1, 2021 as a one-night celebration of one of hip-hop’s most influential groups has evolved into one of The J. Grant Experience’s signature productions. After six unforgettable performances and a brief hiatus, A Tribute to A Tribe Called Quest returns by popular demand to City Winery on September 28 for its 7th performance. Under the musical direction of drummer, producer, and bandleader J. Grant, this immersive concert experience stars Marqueal Jordan, Mz. Keeta, and D2G, backed by an exceptional live band that faithfully recreates the unmistakable sound and energy of A Tribe Called Quest. What truly sets this production apart is its seamless integration of original A Tribe Called Quest music videos, perfectly synchronized with the live band and performers. The result is a one-of-a-kind multimedia experience that blurs the line between concert and cinematic tribute, delivering an unmatched level of production, entertainment, and nostalgia that transports audiences back to the golden era of hip-hop. Whether it’s your first time experiencing the show or your seventh, The J. Grant Experience promises an unforgettable evening celebrating the music, culture, and enduring legacy of the Rock & Roll Hall of Fame icons, A Tribe Called Quest.

from $30

Tue, Sep 29 · 60 shows

City WineryWest Loop
City Winery
7:30pm

Zo! And Tall Black Guy (feat. Debórah Bond)

R&B

City Winery Chicago Presents Zo! And Tall Black Guy live on Tuesday, September 29th at 7:30 PM! When it comes to innovative takes on R&B, you can't go wrong with Zo! & Tall Black Guy and their next-level creations that invoke the genre's classic sound while pushing it forward. So what happens when these two guys collaborate? You get progressive joint albums like Abstractions and their latest offering, Expansions. Their set showcases undeniable chemistry between the musicians while featuring powerhouse vocalist and performer, Debórah Bond. They throw a bit of house and funk into the mix while rounding out their groove with keys, warm synth flourishes and an elastic basslines that will keep you moving all night long. Come experience this high-energy performance and let's celebrate Zo! & Tall Black Guy's Expansions album in Chicago!

from $30

Wed, Sep 30 · 89 shows

Broken HeartsWest Loop
Broken Hearts
8:00pm

Aaron Leese & the Panhandlers

Jazz · Blues

Danceable, upbeat New Orleans roots music and some modern country with a twist. Aaron Leese & the Panhandlers play music for dancing drunks, lost souls, and revolution schemers. Come joins us for an night of deep Americana and southern soul. https://www.facebook.com/ https://www.youtube.com/@AaronLe

City WineryWest Loop
City Winery
7:30pm

Dolly Parton Drag Dinner

City Winery Chicago Presents Dolly Parton Drag Dinner Hosted by Lucy Stoole live on Wednesday, September 30th at 7:30 PM! From Jolene to Islands in the Stream, it's a fabulous afternoon of wigs, brunch, and rhinestone glam. Join us for an afternoon as we celebrate the icon, Dolly Parton. Hosted by Lucy Stoole, presented by Flip Phone Presents.

from $30

French 75 Gallery & LoungeAurora
French 75 Gallery & Lounge
6:30pm

Live Jazz

Jazz

Braden Smith and his quartet, Wednesday nights.

↻ Every week in February, March, April, May, July, August, September, October, November and December on Wednesday

Thu, Oct 1 · 110 shows

93 Octane Brewery - ElmhurstElmhurst
93 Octane Brewery - Elmhurst
6:00pm

Elmhurst Live Music Thursdays at 93 Octane Brewery

Looking for live music in Elmhurst on Thursday nights? 93 Octane Brewery Elmhurst is your go to spot for great music, craft beer, and a high energy taproom experience. Join us every Thursday from 6 to 9 PM for live music in Elmhurst featuring a rotating lineup of local musicians playing everything from acoustic sets to rock, country, and crowd favorites. Whether you are planning a night out in Elmhurst, searching for live music near you, or just looking for things to do on a Thursday night, 93 Octane Brewery delivers the perfect mix of music, drinks, and atmosphere. Enjoy fresh craft beer, a full food menu, and a lively crowd while discovering some of the best live music Elmhurst has to offer. Additional Details: No cover Seating is first come, first served

No cover

FitzGerald'sBerwyn
Amy Lavere
8:30pmSidebar

AMY LAVERE & WILL SEXTON

Alt-country · Rock

AMY LAVERE & WILL SEXTON! Amy LaVere is an acclaimed Memphis based artist, writer, bass player and troubadour. The dark and charming writer has released seven critical

No cover

Half Day Brewing CompanyLincolnshire
Half Day Brewing Company
6:00pm

Live Music Thursdays & Saturdays

Live Music at Half Day Brewing – Thursdays & Saturdays There’s always something happening at Half Day Brewing. Join us all summer long for live music every Thursday evening, plus select Saturday performances featuring talented local artists, great food, cold brews, and an unbeatable atmosphere. Whether you're meeting friends for dinner, enjoying drinks on the patio, or just looking for a fun night out, our live music series is the perfect excuse to stay a little longer. Relax, grab a pint, and enjoy the soundtrack to your summer. Live Music • Great Food • Cold Brews • Better Times. Live music every Thursday evening, 6 to 8pm, plus selected Saturdays.

North & Maple Kitchen + BarTinley Park
John Grace
7:00pm

Grace & John

What's better than a great dinner & live music?! Grace & John will have you singing and dancing! Come out and enjoy some great LIVE Music, delicious food, and refreshing cocktails! Call to reserve your table! 708-468-8181

Schubas TavernLakeview
MARO
8:00pm

MARO

with , ,

Adult contemporary · Rock

SO MUCH HAS CHANGED

Doors 7:30pm

Shirley's Piano BarBarrington
Shirley's Piano Bar
7:00pm

Songwriter Showcase Night

It's a night built for real music lovers: no covers, no filler, just raw, honest performances from artists pouring their hearts into every lyric and melody. Whether you're a longtime fan of live original music or looking to discover your next favorite songwriter, this showcase delivers an evening of

Smoke & MirrorsLogan Square
Loukeman
10:00pm

Loukeman

Outsider house

Thursday, October 1st, 2026 Loukeman \- - - - - - - - - - - - - - - - - - - - - - - 2045 N Milwaukee Ave Chicago, IL

$28.33

Fri, Oct 2 · 51 shows

Broken HeartsWest Loop
Diamondback
9:00pm

Diamondback

Death metal

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

Bub CityRiver North
Bub City
10:00pm

Ryan Michaels Band

Rock · Country

Ryan Michaels is a country, rock, vocalist/guitarist based out of Nashville, TN. Michaels tours around the country and has also played shows on the world-famous historical Broadway strip. Frequently...

City WineryWest Loop
Cassadee Pope
7:30pm

Cassadee Pope

Pop rock · Country pop

City Winery Chicago Presents Cassadee Pope live on Friday, October 2nd at 7:30 PM! Over the last 15 years, Cassadee Pope has been a lot of things to a lot of people: leader of seminal pop- punk band Hey Monday, Season 3 winner of The Voice, Platinum-selling (“Wasting All These Tears”), GRAMMY-nominated ("Think of You,” a duet with Chris Young) country singer/songwriter, ally and activist pushing for social change and a brighter future in a backward world. But through it all – the Warped Tour parking lots, tours with Fall Out Boy and Yellowcard, CMT Awards and chart-topping singles – she’s always remained fearlessly, unapologetically herself. Now, Pope returns with a tremendous sense of freedom guiding her and a forthcoming album set to once again, amplify her confessional writing and redefine her place as a pop-punk mainstay. The future is open wide in ways she previously thought impossible – leaving no doubt she’s exactly where she’s meant to be.

from $36