Zanies brings top touring comedians and local favorites to Old Town every Saturday night. Two-drink minimum. Shows sell out fast — grab tickets early.
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Afro Fusion All White Yacht Cruise
You're stepping onto the Anita Dee II dressed head-to-toe in white, ready to float across Lake Michigan while three levels of DJs spin everything from Amapiano to Afrobeats to dancehall—think less stuffy boat party, more floating festival with the Chicago skyline as your backdrop. The open-air top deck is where the energy peaks, but you'll find seamless vibes throughout, with international talent keeping the rhythm locked in until the sun dips.
Chicago House Music Festival & Conference
Chicago's house music scene birthed a global movement, and this festival brings that legacy front and center with performances that'll have you understanding why this city remains the genre's beating heart. You'll move between main-stage sets and intimate panel discussions where the actual architects of house music break down how four-on-the-floor became four-on-the-world, then network with producers, DJs, and obsessives who actually live this.
Patio Season Kickoff at Big Star
Wicker Parks best patio opens for the season. DJ sets, special taco menu, and frozen margaritas all weekend.