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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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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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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
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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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
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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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.
Add to calendarStumblday's hand-checked ranking of the best music in Downtown, the Loop & West Loop the weekend of Oct 23–25, 2026: 13 picks, refreshed weekly.
