This annual (and free) arts-centric Halloween parade returns to Columbus Drive for an evening of colorful, family-friendly flair. Watch as participants from major cultural organizations, youth programs and aspiring artists march from Balbo Drive to Jackson Boulevard. Arts in the Park is bringing back its "Upside Down" parade in Washington Park on Halloween night, where attendees can walk through a route thronged by costumed performers and puppeteers.
Last updated October 1, 2026: As it turns out, some of the best things in life—or at least, some of the best things to do in Chicago—are free. There are plenty of free ways to spend your time over the next few weeks, including ART on THE MART, Halloween parades, live shows and much more. Plus, don't miss out on all the things to do at the Obama Presidential Center without a ticket that won't cost you a dime. Ready to save some money without sacrificing any fun? Check out more of the best free things to do in Chicago this month.
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