Stumblday's hand-checked ranking of the best things to do in South Loop, Chicago, Downtown, the Loop & West Loop the weekend of Sep 25–27, 2026: 4 picks.
4 picks · checked Sep 21
Radius Chicago, South Loop, Pilsen, West Town & the West SideIan Asher headlines a late Radius show with Nate Band and Kala opening.
Radius Chicago, South Loop, Pilsen, West Town & the West SideIan Asher headlines a late Radius show with Nate Band and Kala opening.
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Park 540, South Loop, Downtown, the Loop & West LoopSpend a Union Park afternoon with African and Caribbean culture, music and food at the joint Festival of Life and JSVFest.
Park 540, South Loop, Downtown, the Loop & West LoopSpend a Union Park afternoon with African and Caribbean culture, music and food at the joint Festival of Life and JSVFest.
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Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsImagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsImagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
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Con Azucar Cafe, South Loop, Downtown, the Loop & West LoopCon Azucar Cafe has enough weekend energy to earn a spot on the board.
Con Azucar Cafe, South Loop, Downtown, the Loop & West LoopCon Azucar Cafe has enough weekend energy to earn a spot on the board.
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