The Armando Diaz

It’s the best comedy show in the city. Created in 1995 by iO alum Armando Diaz, Armando is a historic improvisational form where actors improvise a series of interconnected scenes based on the true stories told from a new guest monologist. Featuring new players, surprise celebrity guests, and more each week, come watch the longest running comedy show in Chicago at its home: iO Theater! Still don’t

More on Monday

74th Annual Chicago Columbus Day ParadeMonday, October 12, 2026; opening ceremony at 12 PM at Dearborn Street and Wacker Drive, then the parade steps off south on Dearborn to Van BurenDearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West LoopOne Day Only

Olivia Rodrigo: The Unraveled Tour – Night TwoMonday, October 12, 2026, 7:00 PMUnited Center, Near West Side, Pilsen, West Town & the West SideTickets via TicketmasterOne Day Only

Also in Lincoln Park, Lakeview & Wrigleyville

Lincoln Park Wine FestOctober 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pmJonquil Park, Lincoln Park, Lakeview & WrigleyvilleGeneral admission from $30One Weekend Only

Jordan Jensen LiveSat, Oct 10, 2026 · 7:30pmThe Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleOne Weekend Only

Music Box of Horrors: Possession, In the Mouth of Madness & Event HorizonSaturday, October 10, 2026, 6:45 PMMusic Box Theatre, Lakeview, Lincoln Park, Lakeview & Wrigleyville$13 for most screeningsOne Day Only

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