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

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

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Things to do around North Side

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Frequently asked questions about North Side

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

The best events to attend this weekend in North 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:
  • REGGAE SUNDAY: The #1 Caribbean Party In The City
  • Afro Fusion Sunday Funday
  • REGGAE SUNDAYS The #1 Caribbean Weekly Party!!! MDW ALL White 5/24/26
  • AFROBEATS SUNDAY - One Night Only (MDW)

    • Which events are currently trending in North Side?

    Trending weekend events in North Side often reflect seasonal moments, nightlife demand, and popular neighborhoods, including concerts, parties, and special themed events. The trending searches this month in North Side are:
  • chicago_events
  • rooftop
  • cafe

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

    In addition to what's happening right now, there are many upcoming weekend events in North Side, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Club Pilates Arboretum Anniversary Weekend May 21–25
  • NO SENIOR CITIZEN HUNGRY! ADOPT A GRANDPARENT FARMER’S MARKET PROGRAM
  • Memorial Day Weekend at Mac’s Wood Grilled
  • Celebration Nights at Red Star Kitchen + Bar

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

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