Things to do in Chicago on Wednesday, October 28, 2026

219 events listed in and around Chicago, each with its time and venue.

Evening

Press Play: a Queer Karaoke Party
Karaoke · 7:30 PM · North Lawndale
Live On Ogden Halloween ( R&B Live Band Karaoke )
Karaoke · R&B / Soul · 8 PM – 1:30 AM · West Loop
EMERGENCY PREGAME: HALLOWEEN
Dance Party · Halloween · 8 PM – 11 PM · Lakeview
Hush Hush Stand Up Comedy Show
Stand-up · 8 PM · Logan Square
Midweek Speed Dating 2.0 in River North | Cityswoon | Ages 47-62
Singles · Dating · 8 PM · River North
Air hockey Emporium Logan square
Game Night · Air Hockey · 8 PM · Logan Square
Creature of the Night Pageant presented by Vanda LaRose & Judith Priest
Drag & Burlesque · Spjork · 8 PM – 11:30 PM · Lakeview
Community Gong Night
Meditation · 8 PM · West Loop
Rock The Mic Wednesdays With Trae Tunes
Karaoke · R&B / Soul · 8 PM – 2 AM · Chatham
Comedians You Should Know: Chicago's Funniest Stand-Up. No Joke
Stand-up · 8 PM · Streeterville
Vic Mensa
Live Music · Hip-Hop / Rap · 8 PM · Near West Side
DoNskI ENT. PRESENTS DA FUNNY PEOPLE #1 OPEN MIC COMEDY SHOW IN CHICAGO!
Comedy Open Mic · 8 PM – 11:30 PM · Little Italy
Phillip Phillips - Let’s Go Far Tour with Katie Lynne Sharbaugh
Live Music · 8 PM · Pilsen
Harrison Presents: Secret Rivalry Rave HALLOONEEN - Chicago
Dance Party · Halloween · 8 PM – 12 AM · Lakeview
Comedy Night at The Charleston
Stand-up · 8:30 PM · Bucktown
ChiTown Drive-In Presents - Halloween (the 1978 Original!)
Film · 8:45 PM · Pilsen
Delicate Steve / Yellow Ostrich
Live Music · 9 PM · Ukrainian Village
Scary-oke
Karaoke · Halloween · 9 PM – 12 AM · Lakeview
Karaoke Night
Karaoke · 9 PM – 12 AM · Lakeview
All things to do in Chicago