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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:
  • The Comedy Roast of Oak Park: Unfiltered, Unplugged, and Totally Roasted
  • Wild Hare Music Presents DJ PAPA G
  • Moms Who Drink and Swear: Mother's Day Weekend Edition at Comedy Plex
  • âš¡ SpeedChicago Dating | Saturday Night Ages 27–42 | Chicago’s Speed Dating

    • 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:
  • mothers day
  • may
  • april events
  • 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:
  • Horton with Linda-Denise Fisher-Harrell | Open Company Class, May 2026
  • Tequila & The Five Elements: Fire • Earth • Water • Air • Spirit
  • ABBA Mamma Mia Drag Dinner
  • Single Malts from Around the World

    • 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