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Free Things to Do in Streeterville, Chicago the Weekend of Oct 9–12, 2026

Stumblday's hand-checked ranking of the best free things to do in Streeterville, Chicago, Downtown, the Loop & West Loop the weekend of Oct 9–12, 2026: 1 pick.

1 picks · checked Sep 21

WhenAll weekendFri nightSaturdaySat nightSundaySun nightColumbus Day
WhereAll ChicagoDowntown, the Loop & West LoopLincoln Park, Lakeview & WrigleyvilleLogan Square, Wicker Park & BucktownPilsen, West Town & the West SideHyde Park, Bronzeville & the South SideAndersonville, Uptown & Lincoln SquareEvanston & Oak ParkFar Suburbs
WhatAllFreeArtMusicMarketsOutdoorsFoodDate night

Planning ahead for Oct 9–12, 2026?

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More this weekend across Chicago

Olivia Rodrigo – The Unraveled TourUnited Center, 1901 W Madison, Pilsen, West Town & the West Side
Chicago Blackhawks vs. Carolina HurricanesUnited Center, 1901 W Madison, Pilsen, West Town & the West Side
Bank of America Chicago MarathonGrant Park, Downtown, the Loop & West Loop
74th Annual Chicago Columbus Day ParadeDearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West Loop
Fall Fest at Lincoln Park ZooLincoln Park Zoo, Lincoln Park, Lakeview & Wrigleyville
Jerry Seinfeld Live!The Chicago Theatre, Downtown, the Loop & West Loop