Stumblday's hand-checked ranking of the best things to do in Streeterville, Chicago, Downtown, the Loop & West Loop the weekend of Oct 2–4, 2026: 2 picks.
2 picks · checked Sep 21
Museum of Contemporary Art Chicago, Streeterville, Downtown, the Loop & West LoopThe Great Art Tailgate with Bad at Sports has enough weekend energy to earn a spot on the board.
Museum of Contemporary Art Chicago, Streeterville, Downtown, the Loop & West LoopThe Great Art Tailgate with Bad at Sports has enough weekend energy to earn a spot on the board.
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Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopKowalski has enough weekend energy to earn a spot on the board.
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopIt lands the Friday before, plus every Friday until then. Unsubscribe anytime.
