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HappeninsChicagoOctober

Things to do in Chicago in October 2026

About 55,000 marathon runners cross 29 neighborhoods on the second Sunday, and Open House Chicago opens around 200 buildings for one free weekend, many of them usually closed to the public.

Follow Chicago in your calendar: Google CalendarApple or Outlook Confirmed dates only. New ones appear on their own.

Starting in October

Expected in October, dates not announced yet

Lincoln Square Apple Fest Community

Lincoln Square Apple Fest

Expected October 2027 N. Lincoln Avenue between Lawrence and Sunnyside avenues, Chicago
Ticketed
Chicago Powwow Community

Chicago Powwow

Expected October 2027 Schiller Woods East, Chicago
Ticketed
Chicago Zine Fest Arts & Culture

Chicago Zine Fest

Expected October 2027 Harold Washington Library Center, Chicago
Free
Historic Pullman House Tour Arts & Culture

Historic Pullman House Tour

Expected October 2027 Pullman Exhibit Hall (ticket pickup), Pullman National Historical Park, Chicago
Ticketed
Chicago Columbus Day Parade Holidays & Parades

Chicago Columbus Day Parade

Expected October 2027 State Street, Wacker Drive to Van Buren Street, Chicago
Ticketed
Open House Chicago Arts & Culture

Open House Chicago

Expected October 2027 Chicago Architecture Center and participating buildings citywide, Chicago
Free
Pilsen Open Studios Arts & Culture

Pilsen Open Studios

Expected October 2027 Pilsen Arts & Community House and studios across Pilsen, Chicago
Ticketed

Already on when October starts

These started in an earlier month and are still running.

Most of the dates here are for October 2027.

5 more run every week in Chicago year round, including Green City Market and Randolph Street Market. See the full calendar.

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