Things to do in Chicago this week

Monday, October 26

• The Best of The Second City
  7:00 PM · Second City-Chicago: Mainstage · Also Oct 31
• Welcome to the Show with Derek Bish
  7:00 PM · Three Top Lounge
• She Wants Revenge
  7:00 PM · House of Blues Chicago · 2 showings
• ChiTown Drive-In Presents - Obsession (2026)
  7:00 PM · ChiTown Movies · Also Oct 27
• Drunk Shakespeare: Drunk Dracula (21+ Event)
  7:00 PM · The Lion Theatre · Daily through Nov 1
• Ordinary Peepholes : NOSFERA2 (Early Show)
  7:00 PM · Empty Bottle · From $29
• Tedeschi Trucks Band: Future Soul 2026 Tour
  7:30 PM · The Chicago Theatre · Also Oct 27
• ChiTown Drive-In Presents - Nightmare on Elm Street
  9:15 PM · ChiTown Movies · Also Nov 1
• Ordinary Peepholes : NOSFERA2 (Late Show)
  9:30 PM · Empty Bottle · From $29
• 2nd Set With The Shout Section Big Band
  Time not listed · Andy's Jazz Club & Restaurant · $20
• 1st Set With The Shout Section Big Band
  Time not listed · Andy's Jazz Club & Restaurant · $20
• Chicago Architecture Center River Cruise Aboard First Lady
  Time not listed · Chicago Architecture Center - First Lady · Daily through Nov 1

Tuesday, October 27

• Balloon Museum | EmotionAir - Art You Can Feel - Chicago
  1:45 PM · The Fields Studios · Daily through Nov 1
• ChiTown Drive-In Presents - Michael
  7:00 PM · ChiTown Movies
• Kokandy Productions Jekyll & Hyde (Chicago)
  7:00 PM · Broadway Playhouse at Water Tower Place · Daily through Nov 1
• EGO DOPPLER and NEXUS Live at Fulton Street Collective
  7:00 PM · Fulton Street Collective
• The Book of Mormon (Chicago)
  7:00 PM · Cadillac Palace · Daily through Nov 1
• Joanne McNally
  7:30 PM · Vic Theatre
• Topdog / Underdog - Tuesday, October 27, 2026 7:30 PM
  7:30 PM · Steppenwolf Theater Company
• Sienna Spiro
  7:30 PM · Riviera Theatre- IL
• The Empty Pockets
  8:00 PM · Garcia's Chicago
• The Second City's: Pandemonium, Please Hold
  8:00 PM · Second City-Chicago: Mainstage · Daily through Nov 1
• Dylan Gossett - Live In Concert
  8:00 PM · The Salt Shed Indoors (Shed)
• It's the Great Pumpkin, Charlie Brown! A Guitar for Guaraldi Tribute
  8:00 PM · Three Top Lounge · From $17

And 4 more on this day in the app.

Wednesday, October 28

• Annual Haunted House Trip
  6:00 PM · Reggies Music Joint
• The Parables Tour with Father Mike Schmitz
  7:00 PM · The Chicago Theatre
• ChiTown Drive-In Presents - Hocus Pocus
  7:00 PM · ChiTown Movies · Also Oct 30
• Hayward - Wednesday, October 28, 2026 7:30 PM
  7:30 PM · Steppenwolf Theater Company
• IL SUONO ORCHESTRA: Rock & Cinema Live at Fulton Street Collective
  7:30 PM · Fulton Street Collective
• Adirondack Chair Circle - Wednesday, October 28, 2026 7:30 PM
  7:30 PM · Steppenwolf Theater Company
• Manifest West, Maxwell Lane, Sitrus Sol
  7:30 PM · Reggies Music Joint
• Shakey Graves w/ Wild Pink
  7:30 PM · Vic Theatre
• Topdog / Underdog - Wednesday, October 28, 2026 7:30 PM
  7:30 PM · Steppenwolf Theater Company
• Wolf & Bear - Ages 17+
  8:00 PM · Subterranean
• Vic Mensa
  8:00 PM · Garcia's Chicago
• Phillip Phillips - Let’s Go Far Tour with Katie Lynne Sharbaugh
  8:00 PM · Thalia Hall · From $46

And 5 more on this day in the app.

Thursday, October 29

• Lecture with Deborah Willis
  1:00 PM · Ferguson Lecture Hall - 600 S. Michigan Ave.
• Chicago Maritime Festival — Chicago Maritime Museum
  6:00 PM · Chicago Maritime Museum
• Nicholas Alexander Blues Band/Joanna Connor Blues Band
  6:00 PM · Kingston Mines - Chicago Blues Center · From $18
• ESTEMAN & DANIELA SPALLA - AMORIO USA TOUR
  6:00 PM · House of Blues Chicago · 2 showings
• Chicago Comedy Club
  6:30 PM · Foundation Room at House of Blues Chicago
• ChiTown Drive-In Presents - Beetlejuce (the Original)!
  7:00 PM · ChiTown Movies
• Ricci Armani
  7:00 PM · The Den Theatre
• Cortisa Star
  7:00 PM · Subterranean
• Halloween Show w/Blueshift Big Band & Abram Collier Nonet @ FSC
  7:30 PM · Fulton Street Collective
• Topdog / Underdog - Thursday, October 29, 2026 7:30 PM
  7:30 PM · Steppenwolf Theater Company
• Hayward - Thursday, October 29, 2026 7:30 PM
  7:30 PM · Steppenwolf Theater Company
• Adirondack Chair Circle - Thursday, October 29, 2026 7:30 PM
  7:30 PM · Steppenwolf Theater Company

And 15 more on this day in the app.

Friday, October 30

• Dom Dolla
  5:00 PM · Navy Pier · Also Oct 31
• Hard Country Honky Tonk with The Hoyle Brothers
  5:30 PM · Empty Bottle
• Halloween Party at Howl at the Moon Chicago
  6:00 PM · Howl at the Moon Chicago
• Periphery - A Pale White Dot US Tour
  6:00 PM · Ramova Theatre
• Shadows on the Street: Haunted Tours of Historic Prairie Avenue — Glessner House
  6:30 PM · Glessner House · Also Oct 31
• Weston Estate
  6:30 PM · Outset · Also Oct 31
• Mike Wheeler Blues Band/Joanna Connor Blues Band
  7:00 PM · Kingston Mines - Chicago Blues Center · From $23 · Also Oct 31
• Fareed Ayaz & Abu Muhammad Qawwali Concert | October 30 — South Asia Institute
  7:00 PM · South Asia Institute
• UAU 2026 FANCON [Playlist #Your Youth] in Chicago
  7:00 PM · Logan Square Auditorium · From $59
• The Winter's Tale
  7:00 PM · The Yard at Chicago Shakespeare · Daily through Nov 1
• Winyah
  7:00 PM · House of Blues Chicago · 2 showings
• Three Floyds 30th Anniversary Event with Pig Destroyer, Necrot, Eternal Champion, and Lair of The Minotaur
  7:00 PM · Bottom Lounge · From $40

And 26 more on this day in the app.

Saturday, October 31

• Carmela Full of Wishes
  9:30 AM · 100 S Racine Ave · Also Nov 1
• Adirondack Chair Circle - Saturday, October 31, 2026 3:00 PM
  3:00 PM · Steppenwolf Theater Company
• Topdog / Underdog - Saturday, October 31, 2026 3:00 PM
  3:00 PM · Steppenwolf Theater Company
• 38th Annual Edgar Allan Poe Readings — Glessner House
  5:00 PM · Glessner House
• Gods of Chaos Halloween
  5:00 PM · Aragon Ballroom
• Depaul Blue Demons Womens Volleyball vs. Creighton Blue Jays Womens Volleyball
  5:00 PM · McGrath Arena
• ChiTown Drive-In Presents - Monsters, Inc.
  6:15 PM · ChiTown Movies
• WITCHES & WIZARDS BALL
  6:30 PM · Foundation Room at House of Blues Chicago
• *SOLD OUT* The Empty Bottle Turns 34 with Post Animal / Gift (Early Show)
  6:30 PM · Empty Bottle · From $40
• Akeem Ali - The Texture Tour
  7:00 PM · House of Blues Chicago · 2 showings
• Fareed Ayaz & Abu Muhammad Qawwali Concert Oct 31 — South Asia Institute
  7:00 PM · South Asia Institute
• Allison Russell w/ Autumn Nicholas
  7:30 PM · Vic Theatre

And 19 more on this day in the app.

Sunday, November 1

• Bruce Liu
  3:00 PM · Symphony Center-IL
• Chicago 1971 - Afternoon Show
  3:00 PM · Carol's Pub · From $17
• Topdog / Underdog - Sunday, November 1, 2026 3:00 PM
  3:00 PM · Steppenwolf Theater Company
• Hayward - Sunday, November 1, 2026 3:00 PM
  3:00 PM · Steppenwolf Theater Company
• Mike Wheeler Blues Band/Omar Coleman Blues Band
  5:30 PM · Kingston Mines - Chicago Blues Center · From $18
• ChiTown Drive-In Presents - Coco
  6:00 PM · ChiTown Movies
• James Tom Goes on a Mini-Tour, Casual Style
  6:30 PM · House of Blues Chicago · 2 showings
• Outlander in Concert
  7:00 PM · The Auditorium
• Chicago 1971 - Evening Show
  7:00 PM · Carol's Pub · From $17
• Murray Hill
  7:15 PM · The Den Theatre
• Bad Gyal
  7:30 PM · Riviera Theatre- IL
• New Constellations: It Comes In Waves Tour with Vox Rea
  7:30 PM · Thalia Hall · From $34

And 4 more on this day in the app.