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Outdoors in Uptown, Chicago Columbus Day Weekend 2026

Hand-picked every week — checked against organizers’ own pages.

Stumblday's hand-checked ranking of the best outdoors in Uptown, Chicago, Andersonville, Uptown & Lincoln Square over Columbus Day weekend 2026 (Oct 10–12): 1 pick.

1 picks · checked Oct 6

Top pick

More this weekend across Chicago

Olivia Rodrigo – The Unraveled TourUnited Center, Pilsen, West Town & the West Side
Chicago Blackhawks vs. Carolina HurricanesUnited Center, 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
Jerry Seinfeld Live!The Chicago Theatre, Downtown, the Loop & West Loop
Fall Fest at Lincoln Park ZooLincoln Park Zoo, Lincoln Park, Lakeview & Wrigleyville