Stumblday's hand-checked ranking of the best free things to do in Downtown, the Loop & West Loop next weekend, Sep 18–20, 2026: 3 picks, refreshed weekly.
3 picks · checked Sep 10
Navy Pier, Streeterville, Downtown, the Loop & West LoopMojnsen · CC BY-SA 4.0 · Wikimedia CommonsCommon, ballet and comedy share Navy Pier’s free festival of Chicago performers across five stages.
Navy Pier, Streeterville, Downtown, the Loop & West LoopMojnsen · CC BY-SA 4.0 · Wikimedia CommonsCommon, ballet and comedy share Navy Pier’s free festival of Chicago performers across five stages.
875 North Michigan Avenue plaza, Magnificent Mile, Downtown, the Loop & West LoopVincent Desjardins from Paris, France · CC BY-SA 4.0 · Wikimedia CommonsSixty artists bring a free outdoor art fair to the plaza and sidewalks at 875 North Michigan Avenue.
875 North Michigan Avenue plaza, Magnificent Mile, Downtown, the Loop & West LoopVincent Desjardins from Paris, France · CC BY-SA 4.0 · Wikimedia CommonsSixty artists bring a free outdoor art fair to the plaza and sidewalks at 875 North Michigan Avenue.
The Palette & Chisel Academy of Fine Arts, Downtown, the Loop & West LoopSee paintings and drawings by 32 artists under 40 in Palette & Chisel’s national emerging-artist showcase.
The Palette & Chisel Academy of Fine Arts, Downtown, the Loop & West LoopSee paintings and drawings by 32 artists under 40 in Palette & Chisel’s national emerging-artist showcase.
