Oct 23, 2025 - Food and Drink
Fall fun: Chicago's best events this weekend
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Experience fall festivities, live music and theatrical performances happening across the city.
- Travel down memory lane with the little ones to catch this '90s classic production on stage.
- 10am and noon Friday at George Van Dusen Theatre at North Shore Center for the Performing Arts in Skokie.
- Tickets start at $15.
- It's your last chance to experience this German celebration with beer, live music, food and outdoor games.
- Times vary, Thursday-Sunday at 171 N. Peoria St. in Fulton Market.
- Tickets start at $19.
- Watch this live performance spotlighting Black art and music.
- 6pm Friday at Harris Theater in Millennium Park.
- Tickets start at $20.
- Catch this Seattle musical group live for a night of funk and R&B, jazz and Afrobeats.
- 8pm Friday at Garcia's in West Loop.
- Tickets start at $20.
- Experience celebrity impersonations of some of the greatest icons like Madonna, Dolly Parton, Beyoncé and more.
- Don't party famished — dinner and brunch are served.
- Times vary Friday-Sunday at Y Bar in River North.
- Tickets start at $35.
- Spend a spooky afternoon sipping tea and champagne at this fancy hotel with small bites and pastries.
- Saturday-Sunday at The Ritz-Carlton off Mag Mile.
- Tickets start at $105.
- The long-running dance party celebrates iconic moments from VMA history before a walk-off for best costumes.
- 9pm Saturday at Sleeping Village in Avondale.
- Tickets start at $20.
- Shop this curated indoor market and support local and small businesses.
- 11am-5pm Saturday-Sunday at Artifact Events in Ravenswood.
- Tickets start at $10.