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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:
  • Trick or Drink: Chicago Halloween Bar Crawl (3 Days)
  • Witch Finger HALLOWEEN w/ Jason Kendig, DJ Heather, Trqpiteca, Harry Cross
  • It’s Bussin’ Halloween Costume Party Juke Vs Hip Hop (Chicago) Hubbard Inn
  • River North Halloween Crawl

    • Which events are currently trending in Chicago?

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

    • 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:
  • 3RD ANNUAL CRAWLLOWEEN: River North Halloween Bar Crawl(5 shots included)
  • Chicago Official Halloween Bar Crawl LIVE! River North and West Loop 2026
  • Haunted Halloween Night Lake Cruise on Friday, October 30th
  • Afrobeats Fridayz @ Masada: Halloween Costume party (Up to $1000 in prizes)

    • 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