$10 Improv Night

All the cool kids stay out late on a school night! Join new teams as they deliver a short and sweet show filled with laughter and improvised comedy in this new incubator for comedy’s rising stars. You can catch brand new kickstart team’s The Etsy Witches and Wet Sox every Monday in May and June at 9pm, performing alongside headliner Blast! Doors: 8:45PM (following Armando) Show: 9:00PM

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

See the full ranked weekend board →