Justin Whitehead at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Justin Whitehead is a rising American stand-up comedian and digital content creator known for his signature improvisational skills, raw storytelling, and viral social media voice-overs. He has built a loyal following of more than 300,000 fans across platforms by blending observational S

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Chicago Bears vs. New York JetsSun, Oct 4, 2026 · 12:00pmSoldier Field, Museum Campus, Downtown, the Loop & West LoopOne Day Only

Maxwell Street Market – season finaleSunday, October 4, 2026, 10am–3pmMaxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West LoopFreeOne Day Only

ACE IN THE HoleSunday 4:15pmGene Siskel Film Center, the Loop, Downtown, the Loop & West LoopOne Day Only

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Also in Downtown, the Loop & West Loop

Play On! — Chicago Shakespeare TheaterSeptember 11–October 18, 2026; selected performancesThe Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopLimited Run

Jack's Pumpkin Pop-UpRunning through November 1Goose Island, 1265 W. Le Moyne St., Downtown Chicago, Downtown, the Loop & West LoopLimited Run

F1 ArcadeOpen this weekend — recently openedF1 Arcade, River North, Downtown, the Loop & West LoopLimited Run

Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime TourRuns through Oct 3, 2026Inside Chicago Walking Tours, Downtown, the Loop & West LoopLimited Run

Bill Burr LiveFriday, October 2, 2026, 7:30 PM; Saturday, October 3, 7:00 PM and 10:00 PMThe Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopOne Weekend Only

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