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Events and Things to do in West Side, Chicago this weekend

Looking for things to do in West Side 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 West Side's most popular events.

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Things to do around West Side

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Frequently asked questions about West Side

What are the best events to attend this weekend in West Side?

The best events to attend this weekend in West Side 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:
  • Chicago Women's Expo | 300+ Shops • Beauty • Fashion • Celebs • DIY
  • Manhattan Vintage | Chicago Edition | October 24 + 25
  • The Inn Crowd at Hubbard
  • 10/25! All NEW Patio Brunch Sunday Funday Series @ AZUL! RSVP

    • Which events are currently trending in West Side?

    Trending weekend events in West Side often reflect seasonal moments, nightlife demand, and popular neighbourhoods, including concerts, parties, and special themed events. The trending searches this month in West Side are:
  • concert

    • Which events are coming up in West Side this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in West Side, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • BIC Durga Pujo 2026
  • IPH's Fall Fest on The Riverwalk w/ Hayrides on the River & More in Chicago
  • West Loop Halloween Bar Crawl 2026
  • 3RD ANNUAL CRAWLLOWEEN: River North Halloween Bar Crawl(5 shots included)

    • Are there free things to do in West Side this weekend?

    Yes — there are often free things to do in West Side 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 West Side this weekend:
  • Free Events this weekend