Chicago, week of October 19, 2026
What's on in Chicago, Monday October 19 to Sunday October 25, 2026: 618 events, 131 of them free. A few picks per kind of event; every event links to its original listing.
618 events 131 free
- Mon Oct 19: 0
- Tue Oct 20: 0
- Wed Oct 21: 0
- Thu Oct 22: 0
- Fri Oct 23: 0
- Sat Oct 24: 0
- Sun Oct 25: 618
More picks, day by day: Tech, AI & startups · Family & kids · Free · Every week · This week
Music 71
- Sun Oct 25 · 3 PM Sleeping Beauty & Dvor??k Cello Concerto Symphony Center-IL
- Sun Oct 25 · 4 PM Speakeasy House Radio: K' Alexi Shelby, Vitigrrl, Marrio Le Nocturne · $15-$22
Comedy 36
Arts, theater & film 199
- Sun Oct 25 · 1 PM THE BOOK OF MORMON Cadillac Palace Theatre
- Sun Oct 25 · 2 PM The Winter's Tale Courtyard Theater at Chicago Shakespeare Theater
Tech, AI & startups 7
- Sun Oct 25 · 10 AM Higher Grounds Andersonville: Deeper Conversations Collectivo Andersonville
- Sun Oct 25 · 6 PM Malarkey Comedy Expo League Malarkey Comedy
Food & drink 46
- Sun Oct 25 · 11 AM Singles Meet Up at The Farmers Market 21-35 and 36-50 October- Chicago Wicker Park Farmers Market · $15.33-$28.81
- Sun Oct 25 · 12 PM Demo & Dine: Ragù Salsiccia e Broccoli Eataly Chicago · $97.87
Nightlife & dancing 51
- Sun Oct 25 · 1 PM Chicago Thriller Rehearsal Traffic Jam! Swing · Free
- Sun Oct 25 · 2 PM Holy Ghost Bingo: God, Goblins, & Games! Stars and Garters
Family & kids 39
- Sun Oct 25 · 10:30 AM Spooky Sing-Along Old Town School of Folk Music
- Sun Oct 25 · 7 PM Balloon Museum | EmotionAir - Art You Can Feel The Fields Studios
Outdoors 11
- Sun Oct 25 · 7 AM Discover Chicago’s hidden gems with a scavenger hunt by World City Trail! Navy Pier · $8.78-$15.70
- Sun Oct 25 · 7:30 AM Sunrise Birding at Jackson Park Jackson Park
Free 123
- Sun Oct 25 · 10 AM Meet Me on Milwaukee (MMoM) Milwaukee Ave from North/Damen to Ashland · Free
- Sun Oct 25 · 1 PM Spooktacular: Clark Street Clark St. · Free
This week is over. The picks are what Chicago Events listed during it; their links go to the original listings, which may have changed since. What’s on now: this week.
Week 2026-W43. Built from Chicago Events’s listings of 2026-11-13; picks favour events several sources list, with a set time and place, over weekly classes and repeating series. Times are local (America/Chicago).