Chicago, week of October 26, 2026
What's on in Chicago, Monday October 26 to Sunday November 1, 2026: 4,603 events, 1,181 of them free. A few picks per kind of event; every event links to its original listing.
4,603 events 1,181 free
- Mon Oct 26: 473
- Tue Oct 27: 650
- Wed Oct 28: 687
- Thu Oct 29: 718
- Fri Oct 30: 697
- Sat Oct 31: 818
- Sun Nov 1: 560
More picks, day by day: Tech, AI & startups · Family & kids · Free · Every week · This week
Music 548
- Mon Oct 26 · 7 PM She Wants Revenge House of Blues Chicago
- Mon Oct 26 · 7:30 PM Tedeschi Trucks Band: Future Soul 2026 Tour The Chicago Theatre
- Tue Oct 27 · 7:30 PM Joanne MCnally: Pinotphile The Vic Theatre
- Tue Oct 27 · 7:30 PM Sienna Spiro Riviera Theatre- IL
- Wed Oct 28 · 7:30 PM Shakey Graves w/ Wild Pink Vic Theatre
- Wed Oct 28 · 7:30 PM Manifest West, Sitrus Sol, Maxwell Lane Reggies Music Joint
Comedy 210
- Tue Oct 27 · 7 PM Casey Rocket Zanies Comedy Club
- Wed Oct 28 · 7 PM DJ Rybski at Zanies Comedy Club Chicago Zanies Comedy Night Club · $101.07
- Wed Oct 28 · 8 PM VOUCH! Comedy Show Laugh Factory
- Thu Oct 29 · 8 PM Brew Comedy: New Material Night at Laugh Factory Chicago Laugh Factory Chicago · $21.41-$28.16
- Sun Nov 1 · 7 PM SUNDAY NOVEMBER 1: CHICAGO'S BEST COMEDY SHOW The Comedy Bar - Chicago Main Stage · Free
- Sun Nov 1 · 7:15 PM MURRAY HILL: Showbiz! Show & Talkback The Den Theatre
Arts, theater & film 1,341
- Mon Oct 26 · 7 PM ChiTown Drive-In Presents - Obsession (2026) ChiTown Movies
- Mon Oct 26 · 7 PM The Best of The Second City Second City-Chicago: Mainstage
- Tue Oct 27 · 7 PM The Book of Mormon (Chicago) Cadillac Palace
- Tue Oct 27 · 7:30 PM Piano Trios: Beethoven, Smetana, and Dvořák Chamber Music Society of Lincoln Center Harris Theater
- Wed Oct 28 · 8 PM Vic Mensa Garcia's Chicago
- Thu Oct 29 · 6 PM ESTEMAN & DANIELA SPALLA - AMORIO USA TOUR House of Blues
Tech, AI & startups 163
- Mon Oct 26 · 4 PM Why AI is our Ultimate Test and Greatest Invitation Chicago Public Library (Chicago Lawn Branch) · Free
- Tue Oct 27 · 8 PM Triage: A Tuesday Industry Night The California Clipper · Free
- Wed Oct 28 · 6 PM General Business Networking - Chicago Hubbard Inn · $0-$22.59
- Wed Oct 28 · 7 PM Startup Networking Chicago: Founders, Investors & Talent Mixer Joy District · $0-$65.85
- Fri Oct 30 · 8 AM 13th Annual Booth-Kellogg Entrepreneurship Through Acquisition Conference Hyatt Regency Chicago
- Fri Oct 30 · 7 PM Nightmare on Fulton Street! mHUB · $10
Food & drink 324
- Tue Oct 27 · 6 PM Hands-On: Pasta Traditions from the North Eataly Chicago · $115.57
- Wed Oct 28 · 7 PM Singles Mixer at Four Seasons Hotel in Chicago! Adorn Bar & Restaurant · $55.85
- Fri Oct 30 · 5 PM Lincoln Park Halloween Crawl Brando's Lincoln Park · $16.25-$23.23
- Fri Oct 30 · 5 PM Chicago Friday and Saturday Halloween Bar Crawl - West Loop - Fri, Oct 30 Esco · $16.25-$59.35
- Sat Oct 31 · 11 AM Bottomless Mimosas on the Riverwalk - Every Saturday in Chicago Island Party Hut (between Lake Shore Drive and Columbus on the Riverwalk) · $25-$31.26
- Sun Nov 1 · 11 AM Lesbian Singles Brunch at Turquoise Cafe 21-35 November-Chicago Turquoise Cafe & Restaurant · $12.51
Nightlife & dancing 701
- Mon Oct 26 · 5:30 PM 2026 3Arts Awards Celebration Harris Theater
- Tue Oct 27 · 7 PM Movie/Music Video Bingo w/ Whaddyaknow Chicago Logan Square
- Tue Oct 27 · 9 PM Tuesday Night Karaoke w/ Grizzy Mack & Jess Chicago Wicker Park
- Sat Oct 31 · 9 PM Graveyard Bash Hosted By: DJ Saggitari House of Blues
- Sat Oct 31 · 11 PM Asian Elements Halloween Night w/ Comrade Dimps Fame Nightclub · Free
- Sun Nov 1 · 8 PM Geese - Getting Killed Again Tour The Salt Shed
Family & kids 382
- Mon Oct 26 · 11:30 AM Trick or Treat on Southport Southport Corridor
- Wed Oct 28 · 8 PM Phillip Phillips - Let’s Go Far Tour with Katie Lynne Sharbaugh Thalia Hall
- Thu Oct 29 · 5:15 PM Tinkering Time: Chess Club West Loop Library · Free
- Thu Oct 29 · 6 PM Balloon Museum | EmotionAir - Art You Can Feel The Fields Studios
- Fri Oct 30 · 6:30 PM Weston Estate Outset
- Fri Oct 30 · 8 PM The Living Tombstone - The Multiplayer Tour Aragon Ballroom
Outdoors 39
- Mon Oct 26 · 7 AM Discover Chicago’s hidden gems with a scavenger hunt by World City Trail! Navy Pier · $8.78-$15.70
- Mon Oct 26 · 10 AM Chicago Riverwalk Secrets Quest Michigan Avenue & East Wacker Place · $23.18
- Wed Oct 28 · 5 PM 2026 Shadow Carriers: Lincoln Park Ghost Tour Chicago History Museum · $37.40
- Thu Oct 29 · 9 AM Future Travel World™ Chicago — International Travel & Experience Show Marriott Marquis Chicago · $187.41-$395.85
- Thu Oct 29 · 6 PM Nature Night Out Peggy Notebaert Nature Museum
- Fri Oct 30 · 2 PM Friday Guided Nature Walks North Pond Gazebo
Free 937
- Mon Oct 26 · 5:30 PM Raj Chetty in Conversation UIC Student Center East · Free
- Mon Oct 26 · 6 PM Game Night Monochrome Brewing · Free
- Wed Oct 28 · 7:30 PM Chicago Fire FC Box Soldier Field · Free
- Wed Oct 28 · 9 PM Karaoke Night Replay Lakeview · Free
- Thu Oct 29 · 5 PM Golden Hour Featuring Philly Peroxide Epiphany Center for the Arts · Free
- Thu Oct 29 · 9 PM Research & Development The California Clipper · 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-W44. 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).