#1
House of Blues Chicago, River North, Downtown, the Loop & West LoopSep 13, 2026–Oct 18, 2026
World Famous Gospel Brunch at House of Blues (CHI)
World Famous Gospel Brunch at House of Blues (CHI) is listed for Chicago this weekend.
Limited Run
Music in Chicago the Weekend of Oct 16–18, 2026
Hand-picked every week — checked against organizers’ own pages.
Stumblday's hand-checked ranking of the best music in Chicago the weekend of Oct 16–18, 2026: 6 picks, refreshed weekly.
6 picks · checked Sep 28
6 picks
The 6 picks
House of Blues Chicago, River North, Downtown, the Loop & West Loop#1Sep 13, 2026–Oct 18, 2026 · Limited Run
House of Blues Chicago, River North, Downtown, the Loop & West LoopWorld Famous Gospel Brunch at House of Blues (CHI)
World Famous Gospel Brunch at House of Blues (CHI) is listed for Chicago this weekend.
Add to calendar#2
Chicago’s First Lady CruisesSep 18, 2026–Oct 18, 2026$50
Chicago By Night River & Lake
Chicago By Night River & Lake is listed for Chicago this weekend.
Limited Run
#2Sep 18, 2026–Oct 18, 2026 · Limited Run
Chicago’s First Lady CruisesChicago By Night River & Lake
Chicago By Night River & Lake is listed for Chicago this weekend.
Add to calendar#3
Inside Chicago Walking Tours, Downtown, the Loop & West LoopSep 18, 2026–Oct 17, 2026
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Limited Run
#3Sep 18, 2026–Oct 17, 2026 · Limited Run
Inside Chicago Walking Tours, Downtown, the Loop & West LoopHaunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Add to calendar#4
House of Blues Chicago, River North, Downtown, the Loop & West Loop#4Friday, October 16, 2026, 7:00 PM · Limited Run
House of Blues Chicago, River North, Downtown, the Loop & West Loop#5
City WineryFriday, October 16, 2026, 7:30 PM–10:30 PM
Bob Schneider Live In Concert
Bob Schneider Live In Concert is listed for Chicago this weekend.
One Day Only
#5Friday, October 16, 2026, 7:30 PM–10:30 PM · One Day Only
City WineryBob Schneider Live In Concert
Bob Schneider Live In Concert is listed for Chicago this weekend.
Add to calendar#6
House of Blues Chicago, River North, Downtown, the Loop & West Loop#6Saturday, October 17, 2026, 6:30 PM · Limited Run
House of Blues Chicago, River North, Downtown, the Loop & West Loop
