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Events and Things to do in Chicago, IL this weekend

Looking for things to do in Chicago this weekend? Explore our real-time listings for the best concerts, nightlife, and food and drink experiences. From seasonal festivals and comedy shows to free activities, find your next plan with our constantly updated feed of Chicago's most popular events.

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Things to do around Chicago

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Frequently asked questions about Chicago

What are the best events to attend this weekend in Chicago?

The best events to attend this weekend in Chicago include concerts, nightlife experiences, seasonal events, food and drink tastings, and live entertainment happening across the city. According to Eventbrite, some of the best events this weekend include:
  • Manhattan Vintage | Chicago Edition | October 24 + 25
  • West Loop Halloween Bar Crawl 2026
  • 3RD ANNUAL CRAWLLOWEEN: River North Halloween Bar Crawl(5 shots included)
  • The Inn Crowd at Hubbard

    • Which events are currently trending in Chicago?

    Trending weekend events in Chicago often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in Chicago are:
  • halloween
  • halloween bar crawl
  • halloween party
  • bollywood

    • Which events are coming up in Chicago this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Chicago, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Latina Expo 2026 – Chicago | Empowerment, Innovation & Community
  • BIC Durga Pujo 2026
  • Chicago's Best 90-Min Architecture Boat Tour on The Chicago River
  • IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago

    • Are there free things to do in Chicago this weekend?

    Yes — there are often free things to do in Chicago this weekend, including live music, cultural events, seasonal activities, and community gatherings. Many events on Eventbrite are free or offer free entry options. These are some free events happening in Chicago this weekend:
  • Free Events this weekend