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Inside Chicago Walking Tours, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour at Inside Chicago Walking.
Inside Chicago Walking Tours, Downtown, the Loop & West LoopHaunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour at Inside Chicago Walking.
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Chicago’s First Lady CruisesChicago’s First Lady Cruises
Chicago By Night River & Lake at Chicago’s First Lady Cruises.
Chicago’s First Lady CruisesChicago By Night River & Lake at Chicago’s First Lady Cruises.
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Chop Shop - IL, 2033 W North Ave, Logan Square, Wicker Park & BucktownLogan Square, Wicker Park & Bucktown
This Wild Life w/ Nate Bergman at Chop Shop - IL.
Chop Shop - IL, 2033 W North Ave, Logan Square, Wicker Park & Bucktown
Joe's on Weed Street Chicago, 940 West Weed St., Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Austin Snell (21+ Event) has enough weekend energy to earn a spot on the board.
Joe's on Weed Street Chicago, 940 West Weed St., Lincoln Park, Lakeview & WrigleyvilleAustin Snell (21+ Event) has enough weekend energy to earn a spot on the board.
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Reggie's Music Joint, 2105 S State St, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Authority Zero w/ Counterpunch at Reggie's Music Joint.
Reggie's Music Joint, 2105 S State St, Downtown, the Loop & West LoopAuthority Zero w/ Counterpunch at Reggie's Music Joint.
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Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Badluv, Dan Vallejo, KR!S Cortez, Freshman at Reggies Bananna's Shack.
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopBadluv, Dan Vallejo, KR!S Cortez, Freshman at Reggies Bananna's Shack.
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Ramova Theatre, 3520 S. Halsted St, Hyde Park, Bronzeville & the South SideHyde Park, Bronzeville & the South Side
Mobb Deep x Talib Kweli (18 and Over) at Ramova Theatre.
Ramova Theatre, 3520 S. Halsted St, Hyde Park, Bronzeville & the South SideMobb Deep x Talib Kweli (18 and Over) at Ramova Theatre.
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Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Cris Jacobs at Garcia's Chicago.
Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West Loop
Hollywood CasinoHollywood Casino
Eli Young Band – Aurora, IL – Live In Concert at Hollywood Casino.
Hollywood CasinoEli Young Band – Aurora, IL – Live In Concert at Hollywood Casino.
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Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Sleeping Beauty & Dvořák Cello Concerto at Orchestra Hall, Symphony Center.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopSleeping Beauty & Dvořák Cello Concerto at Orchestra Hall, Symphony Center.
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Graceland CemeteryGraceland Cemetery
TalkDeath’s Cemetery Scavenger Hunt at Graceland Cemetery and Arboretum at Graceland Cemetery.
Graceland CemeteryTalkDeath’s Cemetery Scavenger Hunt at Graceland Cemetery and Arboretum at Graceland Cemetery.
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City Cruises Chicago – Navy Pier, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
City Cruises Chicago Seadog Haunted River Tour at City Cruises Chicago – Navy Pier.
City Cruises Chicago – Navy Pier, Downtown, the Loop & West LoopCity Cruises Chicago Seadog Haunted River Tour at City Cruises Chicago – Navy Pier.
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Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Maggie Rose at Garcia's Chicago.
Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West Loop
Symphony Center-IL, 220 S. Michigan Ave., Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Sleeping Beauty & Dvor??k Cello Concerto at Symphony Center-IL.
Symphony Center-IL, 220 S. Michigan Ave., Downtown, the Loop & West LoopSleeping Beauty & Dvor??k Cello Concerto at Symphony Center-IL.
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The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Tedeschi Trucks Band – Future Soul 2026 Tour at The Chicago Theatre.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopTedeschi Trucks Band – Future Soul 2026 Tour at The Chicago Theatre.
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Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
The Brokes, St. Marlboro at Reggies Rock Club.
Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West Loop
Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Oh He Dead at Garcia's Chicago.
Garcia's Chicago, 1001 W Washington Blvd, Downtown, the Loop & West Loop
Vic Theatre, 3145 N Sheffield Ave, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Shane Dawson Live! at Vic Theatre.
Vic Theatre, 3145 N Sheffield Ave, Lincoln Park, Lakeview & Wrigleyville
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Silvis, Everyday Fantastic, Om In Gold at Reggies Bananna's Shack.
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopSilvis, Everyday Fantastic, Om In Gold at Reggies Bananna's Shack.
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Vic Theatre, 3145 N Sheffield Ave, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
The Longest Johns at Vic Theatre.
Vic Theatre, 3145 N Sheffield Ave, Lincoln Park, Lakeview & Wrigleyville
Riviera TheatreRiviera Theatre
Thee Phantom and The Illharmonic Orchestra at Riviera Theatre.
Riviera TheatreThee Phantom and The Illharmonic Orchestra at Riviera Theatre.
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Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
William Elliott Whitmore, Meg & the Wheelers at Reggies Rock Club.
Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West LoopWilliam Elliott Whitmore, Meg & the Wheelers at Reggies Rock Club.
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George Van Dusen Theatre at North Shore Center, 9501 Skokie Blvd, Evanston & Oak Park9501 Skokie Blvd, Evanston & Oak Park
La Diosa at George Van Dusen Theatre at North Shore Center.
George Van Dusen Theatre at North Shore Center, 9501 Skokie Blvd, Evanston & Oak Park
NOW Arena, 5333 Prairie Stone Parkway, Far Suburbs5333 Prairie Stone Parkway, Far Suburbs
Rahat Fateh Ali Khan at NOW Arena.
NOW Arena, 5333 Prairie Stone Parkway, Far SuburbsStumblday's hand-checked ranking of the best music in Chicago the weekend of Oct 23–25, 2026: 26 picks, refreshed weekly.
