Date night in Chicago
Evening shows, music, comedy, food and drinks.
Saturday, October 17
420 Frankenstein
$32
Pandemonium, Please Hold
Price: see link
Knox – Chicago – My Midwest Best World Tour
Rising pop/country singer-songwriter Knox (Knox Morris) will perform live in Chicago on Saturday, October 17, 2026, at the House of Blues Chicago.
Price: see link
The Infinite Wrench
Price: see link
Jekyll& Hyde
Price: see link
Ben Schwartz & Friends
Ben Schwartz is bringing his “Ben Schwartz & Friends” tour to Chicago for a night of unscripted improv comedy in the fall of 2026.
Price: see link
Catch Your Breath – Not Broken Enough Tour
Catch Your Breath will perform live in Chicago on Saturday, October 17, 2026, as part of their “Not Broken Enough Tour”.
Price: see link
Reality Detox: The Improv Experience
Price: see link
I am the Wind
Free
Joey Bragg at The Comedy Bar
After wrapping the final season of Disney Channel’s top-rated show, LIV AND MADDIE , Joey Bragg has been incredibly busy establishing himself as a comedic leading man in Hollywood.
$25 – $35
The Second City Improv Social at Sheraton Grand Chicago Riverwalk
Enjoy a 90-minute improv experience with The Second City, plus two cocktails and small bites for $110.
$110
Black Latina (The Play) Comes to Chicago
$15 – $50
Clued In
$25
Suki Waterhouse – The Loveland Tour
Suki Waterhouse will conclude her North American tour in Chicago on Saturday, October 17, 2026.
Price: see link
Judah and The Lion – 2026 Tour
Alternative folk-pop band Judah & The Lion will bring their headline tour to Chicago on Saturday, October 17, 2026.
Price: see link
Topdog/Underdog
Price: see link
Guerrero Leads Fandangos & Enigma Variations
Few contemporary violin concertos have made a splash with audiences like Arturo Márquez’s Fandango , which won a 2024 Latin Grammy.
Price: see link
Dance Theatre of Harlem
Celebrate Arthur Mitchell’s belief that ballet belongs to everyone with New York based Dance Theatre of Harlem, a company internationally acclaimed for redefining what ballet looks like in the 21st century.
Price: see link
Premonitions Inc. at Kermess
Price: see link
The Best of IO
$22
Vladimir
Price: see link
DEATH TOLL: The Halloween Drinking Game Sketch Comedy Show
Price: see link
KING HEDLEY II
$40.00
All at Once — The Seldoms with Timothy Daisy
Chicago-based dance company The Seldoms will kick off its 25th anniversary year at Studio5 Performing Arts Center with the world premiere of the new full-length All at Once, a Cubist-inspired performance work by…
Price: see link
A Dark Wood
$34
Sanctuary Stories
$35.00
Stir Friday Night’s 31st Sketch Comedy Revue
Stir Friday Night, Chicago’s premier and longest-running Asian American and Pacific Islander (AAPI) comedy organization, will return to the stage this fall for a two-night celebration of comedy featuring original…
$20
DETROIT ’67
$40
Grupo Duelo – Gravedad Tour
Grupo Duelo is bringing their Gravedad Tour 2026 to the Rosemont Theatre on Saturday, October 17, 2026.
Price: see link
Sweetest Day Comedy Jam
The Sweetest Day Comedy Jam is coming to Chicago on Saturday, October 17, 2026, at 8:00 PM.
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
D.A.R.E Dropouts
$18
Knock, Knock You There?
Get ready for 90-minutes of sketch comedy that flips classic horror on its head.
$20
Sunday, October 18
I am the Wind
Free
Foos Gone Wild – 2026 Tour
Foos Gone Wild is bringing The FOOS GONE WILD Tour 2026 live to Chicago on Sunday, October 18, 2026, at the House of Blues Chicago.
Price: see link
Jekyll& Hyde
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Calimar White at The Comedy Bar
Originally from St. Petersburg, Florida & currently based in Atlanta, Calimar White (AKA Agent Ratliff) is a hilarious standup comic, actor, influencer & business owner.
$25 – $35
UFO Case Files
$20
Lightly Toasted Standup Showcase
Lightly Toasted is a standup showcase at The Home Comedy Theater in the Lakeview neighborhood of Chicago every third Sunday of the month featuring up and coming and old school Chicago-based comics.
Free
Harold Night
$15
Deep Schwa
$15
Monday, October 19
Jekyll& Hyde
Price: see link
Disney Descendants & Zombies: Worlds Collide
The all-new “ Worlds Collide Concert Tour” brings together the worlds of “ Descendants,” “ZOMBIES,” and for the very first time, “ Camp Rock,” in an unforgettable new arena spectacular.
Price: see link
The Armando Diaz
$17
Best of The Second City
Price: see link
Best of the Second City
Price: see link
Late Nite Mic with Vik Pandya at The Comedy Bar
Vik Pandya is a nationally touring stand up comic based in Chicago.
$25 – $35
Music of the Baroque: Vivaldi & Beyond
Baroque trailblazers Antonio Vivaldi and J. S. Bach launch this journey through the world of 18th-century orchestral music.
Price: see link
$10 Improv Night
$10
Tuesday, October 20
Get Lit: Witch Please
Grab your broomstick and get ready for a night of magic, mischief, and mayhem at Get Lit: Witch Please !
$21.05
CSO Chamber Music: Trillium Ensemble
Hear chamber music at its most intimate and expressive. Haydn’s elegant Piano Trio opens the evening, showcasing the wit and warmth of the composer’s enduring works.
Price: see link
Tuesday Good Show
Free
Jekyll& Hyde
Price: see link
Tomato Throw Show at The Comedy Bar
Join us for the most fun interactive comedy show in Chicago, where the audience determines who’s the funniest (and the most unfunny) by throwing [fake] tomatoes at the stage!
$25 – $30
Topdog/Underdog
Price: see link
Ryan Bingham & The Texas Gentlemen – Chicago – Still Gettin’ Away With It Tour
Grammy and Oscar-winning singer-songwriter Ryan Bingham is bringing his fall leg of the “Still Gettin’ Away With It Tour” to Chicago, Illinois on Tuesday, October 20, 2026.
Price: see link
Write Club Chicago Launches its 17th Season of ‘Live Lit’ at GMan Tavern
Write Club Chicago , announces its combatants competing in its 17th season launch Tuesday, Oct.
$25
Hamlet
A dead king, a hasty remarriage, a ghost walking the battlements — and a brilliant but indecisive prince caught in the middle of it all.
Free
Matt and Ben
Price: see link
Pandemonium, Please Hold
Price: see link
Woman Evolve Presents: Sarah Jakes Roberts (The Rogue Route Tour)
Ticket prices may fluctuate, at any time, based on demand. DOORS OPEN ONE HOUR PRIOR TO SHOW More Info: https://www.auditoriumtheatre.org/events/detail/sarah-jakes-roberts-1566036
Price: see link
Wednesday, October 21
Jekyll& Hyde
Price: see link
Disney Descendants & Zombies: Worlds Collide
The all-new “ Worlds Collide Concert Tour” brings together the worlds of “ Descendants,” “ZOMBIES,” and for the very first time, “ Camp Rock,” in an unforgettable new arena spectacular.
Price: see link
RAD. a fun show.
A RAD alt comedy show, featuring standup, music, sketch, clown, drag, and WEIRD SH*T.
Free
Crowd Work Wednesday at The Comedy Bar
Crowd Work Wednesday is a weekly interactive comedy show where anything can happen—and the audience is part of the act.
$25 – $30
DJ Shadow – Endtroducing 30th Anniversary Tour
DJ Shadow will perform live at The Vic Theatre in Chicago on Wednesday, October 21, 2026.
Price: see link
Play Time
$18
Always, Sometimes, Maybe
Price: see link
BEAT: Belew/Vai/Levin/Bozzio Performing the Music of KING CRIMSON
October 21st, 2026 Following more than 100 acclaimed performances across North and South America, Europe, and Japan, BEAT returns this fall for the last North American tour.
Price: see link
Matt and Ben
Price: see link
Pandemonium, Please Hold
Price: see link
Hooch & Holler Comedy Show
Price: see link
The Orbit
$15
The Fizz Show
$15
The Fizz Show
$15
Thursday, October 22
American Airlines Global Wine Dinner Series: It’s All Greek: Wines of the Islands & Beyond
City Winery presents American Airlines Global Wine Dinner Series: It’s All Greek: Wines of the Islands & Beyond on Thursday, October 22nd at 6:30 PM.
$165.00
Jekyll& Hyde
Price: see link
Stone and Stone: On the Road
Join NYC’s half-gay, half-straight identical twin comedy duo, Stone and Stone, for their Chicago debut!
Price: see link
I am the Wind
Free
OhJay Lamont & Friends at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on the west side of Chicago, started doing stand-up comedy in 2015.
$22 – $25
The Buena Vista Orchestra
The Buena Vista Orchestra is scheduled to perform in Chicago, IL, on Thursday, October 22, 2026.
Price: see link
Maher Zain – USA Tour 2026
Maher Zain is performing live in Chicago on Thursday, October 22, 2026, at The Auditorium Theatre as part of his USA Tour 2026.
Price: see link
Adirondack Chair Circle
Price: see link
Sleeping Beauty & Dvořák Cello Concerto
Price: see link
Jonas Brothers – Rosemont, IL – The Burning Up Tour All Over Again
The Jonas Brothers will perform live at the Allstate Arena in Rosemont, IL, on Thursday, October 22, 2026.
Price: see link
Improv The Play
$20
Sinatra ’56 — Songs for Swingin’ Lovers
Sinatra ’56 — Songs for Swingin’ Lovers is the third chapter in a trilogy of cabaret concerts celebrating Frank Sinatra’s remarkable Capitol-era comeback—and the moment he hit his full, swaggering stride.
$38.00
Vladimir
Price: see link
Set In Chicago – Improvised Spooky Movie Sequels
It’s officially spooky season and there’s no better time to watch a scary movie.
$20
Natan Badalov presents: Community Service – A Comedy Show
In his new show, Natan Badalov (Netflix, New York Comedy Festival) explores growing up Bukharian in New York and American Jewish life.
$29.21
A Dark Wood
$34
Matt and Ben
Price: see link
Tartuffe
$25
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
swedm® – Chicago, IL – 2027 North American Tour
swedm® has officially added a Chicago date to their debut North American tour on Thursday, October 22, 2026 .
Price: see link
Give It 2 Me Gay
Give It To Me Gay is a variety show, celebrating queer art and joy through many forms of comedy and performance.
$20.00
Sketch Playlist
Price: see link
Blueprint
$13
Friday, October 23
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
Jekyll& Hyde
Price: see link
Randy Feltface – Gimmick Tour
Australian comedian Randy Feltface is scheduled to perform in Chicago on Friday, October 23, 2026, as part of his “Gimmick” tour.
Price: see link
Omar
Price: see link
Reality Detox: The Improv Experience
Price: see link
Rebecca Black – Chicago – Exhibitionism on Tour
Pop icon Rebecca Black is bringing her “Exhibitionism on Tour” to Chicago, Illinois on Friday, October 23, 2026.
Price: see link
Adam Ray – Chicago – Who Is Me Tour
Comedian and actor Adam Ray will perform live in Chicago on Friday, October 23, 2026, at 7:00 PM.
Price: see link
The Book Of Mormon
Price: see link
I am the Wind
Free
Zar the Star at The Comedy Bar
Zar the Star is a New York City-based stand-up comedian and content creator whose sharp wit, bold storytelling, and unfiltered takes have made her one of the most exciting new voices in comedy.
$25 – $30
Devil’s Daughter
$22
Tedeschi Trucks Band – Future Soul 2026 Tour
Price: see link
Patrick Droney – The Made You Look Tour
Patrick Droney is bringing his brand new fall headlining trek, “The Made You Look Tour,” to Chicago’s Park West on Friday, October 23, 2026.
Price: see link
Topdog/Underdog
Price: see link
Adirondack Chair Circle
Price: see link
Premonitions Inc. at Kermess
Price: see link
Devil’s Daughter
$22
Vladimir
Price: see link
DEATH TOLL: The Halloween Drinking Game Sketch Comedy Show
Price: see link
KING HEDLEY II
$40.00
A Dark Wood
$34
DETROIT ’67
$40
Tartuffe
$25
Devil’s Daughter
$20
Sammy Rae & The Friends – The Album Tour
Sammy Rae & The Friends are scheduled to perform in Chicago on Friday, October 23, 2026, as part of “The Album Tour”.
Price: see link
Menudo – 50th Anniversary Tour
Legendary Latin pop boy band Menudo will perform live at the Rosemont Theatre near Chicago on Friday, October 23, 2026.
Price: see link
Eli Young Band – Aurora, IL – Live In Concert
The Eli Young Band is performing live in Aurora, Illinois, on Friday, October 23, 2026, at 8:00 PM.
Price: see link
PLAYGRND Series – Chicago, IL – City Love Tour
The PLAYGRND Series is bringing its “City Love Tour” to Chicago on Friday, October 23, 2026.
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Yousuke Yukimatsu – Autumn 2026 Tour
Yousuke Yukimatsu (¥ØUUK€ ¥UK1MATU) is scheduled to perform live in Chicago, Illinois on Friday, October 23, 2026, as part of his Autumn 2026 Tour.
Price: see link
Zar the Star at The Comedy Bar
Zar the Star is a New York City-based stand-up comedian and content creator whose sharp wit, bold storytelling, and unfiltered takes have made her one of the most exciting new voices in comedy.
$25 – $30
The Ass Menagerie Presents: FRIGHT CLUB
This Halloween Show is 21+ The first rule of Fright Club is: you’re already in it.
$30
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Hitch*Cocktails
$20
Saturday, October 24
The Wrecks – Finally : OUTSIDE Tour
Alternative rock band The Wrecks will bring their national fall headline run, the “Finally : OUTSIDE Tour,” to the House of Blues Chicago on Saturday, October 24, 2026.
Price: see link
420 Frankenstein
$32
Garam Masala Comedy Dating Show: Shacking Up in Chicago
Two South Asian singles meet for the first time on a blind date on stage, and a live audience watches every awkward, funny and unexpectedly honest moment.
Ticketed, price at link
“Hollywood Hit” at Dinner Detective Chicago
The Dinner Detective is an interactive comedic true crime dinner theatre experience based on real cold cases.
$75.95
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
Jekyll& Hyde
Price: see link
Reality Detox: The Improv Experience
Price: see link
I am the Wind
Free
Zar the Star at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Zar the Star is a New York City-based stand-up comedian and content creator whose sharp wit, bold…
$25 – $35
University Symphony Orchestra: Annual Halloween Concerts
Pictures of the Imagination Colorful, exuberant, and sometimes scary musical pictures by Franz Liszt, Anatol Liadov, and George Whitefield Chadwick spur the imagination – and the creative choreography of the Hyde…
Free
Clued In
$25
Tedeschi Trucks Band – Future Soul 2026 Tour
Price: see link
Blondshell – Scaring Strangers Tour
Blondshell is scheduled to perform live in Chicago, Illinois on Saturday, October 24, 2026, as part of her newly announced “Scaring Strangers Tour”.
Price: see link
Memphis The Musical
Memphis the Musical is a high-energy Broadway musical featuring music by David Bryan and a book and lyrics by Joe DiPietro.
Price: see link
Memphis The Musical
Memphis is a musical with music by David Bryan, lyrics by David Bryan and Joe DiPietro, and a book by Joe DiPietro.
Price: see link
Don Giovanni
Price: see link
Edward Scissorhands In Concert
Released in 1990 and directed by Tim Burton (Beetlejuice, Disney Tim Burton’s The Nightmare Before Christmas), the film centers on Edward (Johnny Depp), a gentle artificial man with scissors for hands.
Price: see link
Topdog/Underdog
Price: see link
Adirondack Chair Circle
Price: see link
Sleeping Beauty & Dvořák Cello Concerto
Price: see link
Thee Phantom and The Illharmonic Orchestra
Thee Phantom and The Illharmonic Orchestra will perform live at the Riviera Theatre in Chicago, Illinois, on October 24, 2026.
Price: see link
Premonitions Inc. at Kermess
Price: see link
The Best of IO
$22
Vladimir
Price: see link
DEATH TOLL: The Halloween Drinking Game Sketch Comedy Show
Price: see link
Halloweensteen 2026 – Chicago, IL
The popular annual rock celebration Halloweensteen is returning to Chicago on Saturday, October 24, 2026.
Price: see link
KING HEDLEY II
$40.00
A Dark Wood
$34
DETROIT ’67
$40
Tartuffe
$25
Lupillo Rivera – 90’s CORRIDOS TOUR
Lupillo Rivera is bringing his 90’s CORRIDOS TOUR to the Rosemont Theatre on Saturday, October 24, 2026.
Price: see link
Best of the Second City
Price: see link
CircuitMOM & Uncle Present: Haunted Hollywood
CircuitMOM Productions has announced its signature Halloween event, CircuitMOM & Uncle Present: Haunted Hollywood, taking place at the House of Blues Chicago on Saturday, October 24, 2026.
Price: see link
Zar the Star at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Zar the Star is a New York City-based stand-up comedian and content creator whose sharp wit, bold…
$25 – $35
University Symphony Orchestra: Annual Halloween Concerts
Pictures of the Imagination Colorful, exuberant, and sometimes scary musical pictures by Franz Liszt, Anatol Liadov, and George Whitefield Chadwick spur the imagination – and the creative choreography of the Hyde…
Free
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
D.A.R.E Dropouts
$18
Sunday, October 25
I am the Wind
Free
Premonitions Inc. at Kermess
Price: see link
Malarkey Comedy Expo League
Welcome to Expo League, where competition and exhibition meet to make an entertaining and interactive experience you’ll never forget!
$10
Jekyll& Hyde
Price: see link
The Longest Johns Live In Concert
The Longest Johns are performing live in Chicago on Sunday, October 25, 2026, at The Vic Theatre.
Price: see link
Sleeping With Sirens – An Ending In Itself Tour
Alternative rock band Sleeping With Sirens will bring their headline An Ending In Itself Tour to Chicago on Sunday, October 25, 2026.
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Brett Goldstein – Chicago, IL – Sex, Death & Small Talk Tour
Brett Goldstein is bringing his brand-new stand-up comedy tour, “Sex, Death & Small Talk,” to Chicago on Sunday, October 25, 2026, at 7:00 PM.
Price: see link
Harold Night
$15
Matt and Ben
Price: see link
Matt Rife Live In Chicago – Stay Golden 2025-26 World Tour
Comedian Matt Rife will perform live at Chicago’s United Center on Oct.
Price: see link
Improvised DCOM
Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM!
$15
Deep Schwa
$15
Monday, October 26
The Armando Diaz
$17
Best of The Second City
Price: see link
Best of the Second City
Price: see link
Late Nite Mic with Vik Pandya at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring stand up comic based in Chicago.
$22 – $25
Tedeschi Trucks Band – Future Soul 2026 Tour
Price: see link
DETROIT ’67
$40
Matt and Ben
Price: see link
She Wants Revenge – 2026 Tour
She Wants Revenge is performing at the House of Blues Chicago on Monday, October 26, 2026.
Price: see link
$10 Improv Night
$10
Tuesday, October 27
SiM – Hooman After All World Tour
Japanese reggae-punk and metal band SiM is scheduled to perform live in Chicago, Illinois on Tuesday, October 27, 2026, as part of their newly announced “Hooman After All World Tour.”
Price: see link
Tuesday Good Show
Free
The Book Of Mormon
Price: see link
Guy’z Nite Comedy Show at The Comedy Bar
Guy’z Nite is a wildly known weekly sold out comedy show headlined by Guy Reuven , starring NEW celebrity lineups of Hollywood’s BIGGEST comedians including Ismo, Michael Blaustein, Shang Forbes and many more Special…
$25 – $30
Tedeschi Trucks Band – Future Soul 2026 Tour
Price: see link
Joanne Mcnally – Pinotphile Tour
Joanne McNally is performing live in Chicago on Tuesday, October 27, 2026, as part of her hotly anticipated new North American stand-up comedy tour, “Pinotphile”.
Price: see link
Sienna Spiro – My House Tour
Sienna Spiro is performing live in Chicago on Tuesday, October 27, 2026, at The Riviera Theatre as part of her massive My House Tour world trek.
Price: see link
Piano Trios: Beethoven, Smetana, and Dvořák Chamber Music Society of Lincoln Center
The piano trio has long offered composers a direct and personal means of expression, and this program brings together three works that reveal the form from different perspectives.
Price: see link
Topdog/Underdog
Price: see link
Matt and Ben
Price: see link
Pandemonium, Please Hold
Price: see link
Comic Court: Chicago’s #1 Comedy Court Show
Order in the court! Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM.
$8
Wednesday, October 28
HACK JOB, A Comedy Show
HACK JOB COMEDY A biweekly showcase of Chicago’s best comedians at Blind Barber in Fulton Market!
$10
Omar
Price: see link
Father Mike Schmitz – Parables: A Time of Reflection
Father Mike Schmitz will bring his popular live presentation, Parables: A Time of Reflection, to The Chicago Theatre in Chicago, Illinois, on Wednesday, October 28, 2026.
Price: see link
The Book Of Mormon
Price: see link
Chicago’s Best Comedy Show at The Comedy Bar
Join Chicago’s best comedians for a hilarious night of stand-up comedy, pizza, and nonstop laughs!
$25 – $35
Shakey Graves – Fondness, Etc. Tour
Shakey Graves will bring his Fondness, Etc. Tour to Chicago on Wednesday, October 28, 2026.
Price: see link
Topdog/Underdog
Price: see link
Adirondack Chair Circle
Price: see link
Play Time
$18
Always, Sometimes, Maybe
Price: see link
Eros Ramazzotti – Una Storia Importante World Tour
Eros Ramazzotti is bringing his Una Storia Importante World Tour to the Rosemont Theatre on Wednesday, October 28, 2026.
Price: see link
Pandemonium, Please Hold
Price: see link
Hooch & Holler Comedy Show
Price: see link
The Orbit
$15
The Fizz Show
$15
The Fizz Show
$15
Thursday, October 29
IMAGINE U: Grace and the Butterfly Effect
Price: see link
The Book Of Mormon
Price: see link
I am the Wind
Free
OhJay Lamont & Friends at The Comedy Bar
OhJay Lamont, born and raised on the west side of Chicago, started doing stand-up comedy in 2015.
$25 – $30
The Airborne Toxic Event
Orchestral indie rock band The Airborne Toxic Event is scheduled to perform live in Chicago, Illinois on Thursday, October 29, 2026.
Price: see link
Dweezil Zappa – DZ20: Like Father, Like Son Tour
Dweezil Zappa is performing live in Chicago on Thursday, October 29, 2026, as a premier stop on his newly announced North American run, “DZ20: Like Father, Like Son Tour”.
Price: see link
Topdog/Underdog
Price: see link
Adirondack Chair Circle
Price: see link
Brahms Requiem
Price: see link
Wait Wait…Don’t Tell Me
Price: see link
Premonitions Inc. at Kermess
Price: see link
Improv The Play
$20
Vladimir
Price: see link
Set In Chicago – Improvised Spooky Movie Sequels
It’s officially spooky season and there’s no better time to watch a scary movie.
$20
Jerker, or The Helping Hand
$30.00
A Dark Wood
$34
Tartuffe
$25
Dresden Dolls – 25th-Anniversary Tour
Dark cabaret duo The Dresden Dolls will bring their 25th-anniversary tour to Chicago on Thursday, October 29, 2026.
Price: see link
Alicia Villarreal – Bendita Locura Tour
Mexican Regional and Latin Pop icon Alicia Villarreal will perform live in Chicago on Thursday, October 29, 2026, as part of her newly announced Bendita Locura Tour.
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Give It 2 Me Gay
Give It To Me Gay is a variety show, celebrating queer art and joy through many forms of comedy and performance.
$20.00
Sketch Playlist
Price: see link
Andy Cohen – Chicago, IL – Twenty Years of the Real Housewives and Bravoverse Tour
Emmy Award-winning host and reality TV mogul Andy Cohen will perform live in Chicago on Thursday, October 29, 2026, at the Athenaeum Center for Thought & Culture.
Price: see link
Blueprint
$13
Friday, October 30
Periphery – A Pale White Dot North America Tour
Periphery is performing live in Chicago on Friday, October 30, 2026, as part of their newly announced “A Pale White Dot North America Tour”.
Price: see link
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
The Last Word
The Last Word is the first 4 course craft cocktail progression paired with a screenplay.
Price: see link
Winyah – 2026 Tour
Winyah is scheduled to perform at the House of Blues Chicago on Friday, October 30, 2026.
Price: see link
Don Giovanni
Price: see link
Reality Detox: The Improv Experience
Price: see link
Sanctum Dark Music Festival 2026
The Sanctum Dark Music Festival returns to Chicago for Halloween weekend on Friday, October 30, and Saturday, October 31, 2026.
Price: see link
The Book Of Mormon
Price: see link
I am the Wind
Free
Romeo & Juliet
The Olde School Shakespeare Collective presents ROMEO & JULIET The Olde School Shakespeare Collective is bringing Shakespeare’s most famous pair of star-crossed lovers to Chicago for three performances this fall.
$20
Devil’s Daughter
$22
D.L. Hughley & Don Lemon – DL + DL: Anything Goes Tour
D.L. Hughley and Don Lemon are bringing their extended national tour, “DL + DL: Anything Goes,” to The Chicago Theatre on Friday, October 30, 2026.
Price: see link
Topdog/Underdog
Price: see link
Adirondack Chair Circle
Price: see link
Premonitions Inc. at Kermess
Price: see link
Devil’s Daughter
$22
Vladimir
Price: see link
DEATH TOLL: The Halloween Drinking Game Sketch Comedy Show
Price: see link
8Turn – Chicago, IL – 2026 2nd World Tour [8TURN TRACE]
The dynamic K-pop boy band 8Turn is bringing their 2026 2nd World Tour [8TURN TRACE] to the Vic Theatre in Chicago.
Price: see link
KING HEDLEY II
$40.00
“The Last Word,” an Adventure Screenplay with a Cocktail Experience
The Last Word , created by Declan Grogan , announces extension performance dates each month from September to December, at the iO Theater, 1501 N.
$20 – $50
Jerker, or The Helping Hand
$30.00
A Dark Wood
$34
DETROIT ’67
$40
Tartuffe
$25
Devil’s Daughter
$20
Maná – Vivir Sin Aire Tour
Legendary Mexican rock band Maná will perform in Rosemont, Illinois, on Friday, October 30, 2026, at the Allstate Arena as part of their “Vivir Sin Aire Tour”.
Price: see link
The Living Tombstone – The Multiplayer Tour
The Living Tombstone is bringing “The Multiplayer Tour” to Dallas on Friday, May 15, 2026.
Price: see link
Grupo Niche – Niche Disco Tour
Grupo Niche is bringing their “Niche Disco Tour” to the Rosemont Theatre on Friday, October 30, 2026.
Price: see link
Amble – 2026 North American Tour
The Irish contemporary-folk trio Amble is performing at The Riviera Theatre in Chicago on Friday, October 30, 2026.
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Hitch*Cocktails
$20
Saturday, October 31
Gods of Chaos Halloween: OsamaSon, Waka Flocka Flame & 2slimey
The second annual Gods of Chaos festival will take over the Byline Bank Aragon Ballroom in Chicago on Halloween night—Saturday, October 31, 2026.
Price: see link
420 Frankenstein
$32
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
Akeem Ali – The Texture Tour
Akeem Ali is performing at the House of Blues Chicago on Saturday, October 31, 2026, for “The Texture Tour.”
Price: see link
Reality Detox: The Improv Experience
Price: see link
Sanctum Dark Music Festival 2026
The Sanctum Dark Music Festival returns to Chicago for Halloween weekend on Friday, October 30, and Saturday, October 31, 2026.
Price: see link
Haunted House Party at Shedd Aquarium
Join Shedd Aquarium for a frightfully fun night at Haunted House Party , where house music and Halloween collide.
Price: see link
I am the Wind
Free
The Niceties
$33.00
Sergei Putinski at The Comedy Bar
Born beneath the Kremlin and rumoured to be Vladimir Putin’s nephew, Sergei Putinski is a man who has seen things you wouldn’t believe — mostly because they happened in 1987 and are no longer relevant.
$30 – $35
Clued In
$25
The Rocky Horror Picture Show
THE ROCKY HORROR PICTURE SHOW returns to The Chicago Theatre on Halloween night!
Price: see link
Topdog/Underdog
Price: see link
Adirondack Chair Circle
Price: see link
Brahms Requiem
Price: see link
Allison Russell – Chicago, IL – The In The Hour of Chaos Tour
Allison Russell will perform live at The Vic Theatre in Chicago, Illinois, on Saturday, October 31, 2026.
Price: see link
Premonitions Inc. at Kermess
Price: see link
The Best of IO
$22
DEATH TOLL: The Halloween Drinking Game Sketch Comedy Show
Price: see link
KING HEDLEY II
$40.00
Jerker, or The Helping Hand
$30.00
DETROIT ’67
$40
Tartuffe
$25
Arcangel – La 8va Maravilla World Tour
Arcángel is performing live in Rosemont on Saturday, October 31, 2026, as part of his “La 8va Maravilla World Tour 20 Aniversario”.
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Rod Wave – Don’t Look Down Tour
Rod Wave is scheduled to perform live in Chicago, Illinois on Saturday, October 31, 2026, as part of his newly announced Don’t Look Down Tour.
Price: see link
Terror in the Tropics: Midnight in Mexico
This Halloween, Three Dots and a Dash is taking over Salon 61 for Terror in the Tropics: Midnight in Mexico, a one-night-only celebration of Mexico’s cocktail scene.
$99
GOOFAZZ Halloween Comedy Show at The Comedy Bar
Stand up comedian, Ohjay Lamont , is a Comedy Bar favorite.
$30 – $35
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
D.A.R.E Dropouts
$18
Knock, Knock You There?
Get ready for 90-minutes of sketch comedy that flips classic horror on its head.
$20
Sunday, November 1
I am the Wind
Free
HighQ
Is it a cannabis-themed game show or an uproarious, electively interactive live theatrical experience?
$15.00
James Tom – Chicago, IL – Goes on a Mini-Tour, Casual Style
Widely discussed performer James Tom will bring his “Goes on a Mini-Tour, Casual Style” show to Chicago on Sunday, November 1, 2026.
Price: see link
Outlander In Concert
Experience the official “Outlander” in-concert event! A live orchestra performs Bear McCreary’s acclaimed score, curated by showrunner Matthew B.
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
UFO Case Files
$20
Joel James at The Comedy Bar
Joel James is anationally touring stand-up comedian, social media entertainer, and self-published cookbook author.
$25 – $35
Bad Gyal – Más Cara World Tour
Bad Gyal will perform at the Riviera Theatre in Chicago on Sunday, November 1, 2026, as part of her “Más Cara World Tour”.
Price: see link
L7 – The Last Hurrah Tour
L7 is bringing “The Last Hurrah Tour 2026” to The Vic Theatre on Sunday, November 1, 2026.
Price: see link
Harold Night
$15
New Constellations – Chicago, IL – It Comes In Waves Tour
The dream pop and synthwave duo New Constellations is scheduled to perform live in Chicago on Sunday, November 1, 2026, at 7:30 PM.
Price: see link
Rod Wave – Don’t Look Down Tour
Rod Wave is scheduled to perform live in Chicago, Illinois on Sunday, November 1, 2026, as part of his newly announced Don’t Look Down Tour.
Price: see link
Deep Schwa
$15
Monday, November 2
The Armando Diaz
$17
Best of The Second City
Price: see link
Best of the Second City
Price: see link
Late Nite Mic with Vik Pandya at The Comedy Bar
Vik Pandya is a nationally touring stand up comic based in Chicago.
$25 – $35
Monday Night PlayGround
PlayGround-Chicago presents Season 5 MONDAY NIGHT PLAYGROUND November 2, 2026, 7pm CT NEW VENUE: The Den & Simulcast Topic: AMERICA 250: The Dreamers, The Builders & The Leaders Admission-Free (Suggested Donation:…
Free
HERE: for the holidays
A fitting show the night before the Midterm Elections— HERE: for the holidays on Monday, November 2 at 7:30PM at The Newport Theater; an innocently lascivious performance, intent on sharing the true meaning of the…
$25 – $35
Jerker, or The Helping Hand
$30.00
$10 Improv Night
$10
Tuesday, November 3
Tuesday Good Show
Free
Tomato Throw Show at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun interactive comedy show in Chicago, where the audience determines who’s the…
$22 – $25
Adirondack Chair Circle
Price: see link
The Blasting Company – Over the Garden Wall Tour
Los Angeles-based nouveau-folk group The Blasting Company is bringing its third annual autumn tour to Chicago, Illinois, on Tuesday, November 3, 2026, at The Vic Theatre.
Price: see link
A Quiet End
sSaged reading of Robin Swados’ deeply human drama about three gay men living together during the early years of AIDS.
Free
Pandemonium, Please Hold
Price: see link
Wednesday, November 4
sombr – You Are The Reason Tour
sombr is bringing his You Are The Reason Tour to Chicago on Wednesday, November 4, 2026.
Price: see link
Chicago’s Best Comedy Show at The Comedy Bar
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St.
$22 – $25
Eivør – 2026 North American Tour
Eivør is bringing her Nordic folk and ethereal sound to Park West in Chicago on Wednesday, November 4, 2026.
Price: see link
Blade Runner – Live In Concert
Blade Runner Live will come to The Chicago Theatre on November 4.
Price: see link
Scott Bradlee’s Postmodern Jukebox – The Future Is Vintage Tour
Scott Bradlee’s Postmodern Jukebox is performing at The Vic Theatre in Chicago on Wednesday, November 4, 2026, as part of “The Future Is Vintage World Tour”.
Price: see link
Adirondack Chair Circle
Price: see link
Play Time
$18
Always, Sometimes, Maybe
Price: see link
Pandemonium, Please Hold
Price: see link
Hooch & Holler Comedy Show
Price: see link
The Orbit
$15
The Fizz Show
$15
The Fizz Show
$15
Thursday, November 5
Abbie Gamboa – Chicago, IL – Have You Ever Looked Around Tour
Christian worship singer and songwriter Abbie Gamboa is bringing her live concert experience to Chicago, Illinois, on Thursday, November 5, 2026, performing at the House of Blues Chicago.
Price: see link
Court Convening 1: America@250
In the wake of the 2026 midterm elections and as part of its America@250 programming , Court Theatre inaugurates its first annual Court Convening, inviting artists, activists, and scholars to debate the importance of…
Price: see link
Pigeons Playing Ping Pong – Fall Tour 2026
Pigeons Playing Ping Pong are performing live in Chicago on Thursday, November 5, 2026, at The Vic Theatre.
Price: see link
Ify Nwadiwe at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Ify Nwadiwe has a whole lot of hyphens!
$25 – $35
Maggie Winters & Friends
Maggie Winters is coming back to where it all began for a one-night-only stand-up showcase.
$30
iO 45th Anniversary Thursday 1-Day Pass
In 1981, iO Theater started a revolution that shaped modern comedy and launched the sharpest, funniest voices in the industry.
$30
Pouya – Foreverglades Tour
Pouya is scheduled to perform live in Chicago on Thursday, November 5, 2026, at The Riviera Theatre as part of The Forever Glades Tour 2026.
Price: see link
Beethoven 5 & Mao Fujita
Price: see link
73 Seconds
Price: see link
Wait Wait…Don’t Tell Me
Price: see link
Improv The Play
$20
Vladimir
Price: see link
Chicago Repertory Ballet: The Capulets
Price: see link
Jerker, or The Helping Hand
$30.00
Sophia Bush: A Life in Progress
Join actress and activist Sophia Bush for an intimate evening of unflinchingly honest storytelling.
$77
KATSEYE – The Wildworld Tour
KATSEYE will bring The Wildworld Tour to Chicago on Thursday, November 5, 2026.
Price: see link
Joey Diaz – 62 & Still Slinging Tour
Joey Diaz is performing live in Chicago on Thursday, November 5, 2026, at The Chicago Theatre.
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Trippie Redd – Chicago, IL – The Non-disclosure Agreement Tour
Rapper Trippie Redd is bringing “The Non-disclosure Agreement Tour” to Chicago in support of his latest album, #NDA.
Price: see link
Roast Battle at Zanies
Roast Battle Is @ Zanies Chicago! From the hit Comedy Central series, Roast Battle, brought to you by the team with over 200,000 online followers, Roast Battle Chicago is at Zanies!
Price: see link
Sophomoric Songs
$20
Blueprint
$13
Friday, November 6
Basement – Chicago, IL – 2026 North American Tour
British indie rock/post-hardcore band Basement will perform live in Chicago, Illinois on Friday, November 6, 2026.
Price: see link
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
Bert Kreischer – Permission To Party World Tour
Bert Kreischer is bringing the Permission To Party World Tour to Chicago on Friday, November 6, 2026.
Price: see link
The Apiary
$30
Reality Detox: The Improv Experience
Price: see link
Rachel Scanlon Live
Stand-up comedian Rachel Scanlon will be performing live in Chicago on Friday, November 6, 2026, at 7:00 PM at Park West.
Price: see link
Pandji Pragiwaksono at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Pandji Pragiwaksono Wongsoyudo is an Indonesian stand-up comedian and entertainment innovator who…
$25 – $35
iO 45th Anniversary Friday 1-Day Pass
In 1981, iO Theater started a revolution that shaped modern comedy and launched the sharpest, funniest voices in the industry.
$30
Devil’s Daughter
$22
Justin Silva – Sorta Rican Tour
Justin Silva is performing live in Chicago on Friday, November 6, 2026, at The Vic Theatre.
Price: see link
Sleep – 2026 North American Tour
The stoner rock/doom metal band Sleep will perform live at The Riviera Theatre in Chicago on Friday, November 6, 2026, as part of their North American tour.
Price: see link
Adirondack Chair Circle
Price: see link
73 Seconds
Price: see link
Premonitions Inc. at Kermess
Price: see link
Devil’s Daughter
$22
Vladimir
Price: see link
Year One
$25
KING HEDLEY II
$40.00
Chicago Repertory Ballet: The Capulets
Price: see link
Peter Pan
$5 – $30
Jerker, or The Helping Hand
$30.00
The Snow Queen
$25.00
Devil’s Daughter
$20
Pedro Fernández – Rosemont, IL – Ave Fénix Two’r
Pedro Fernández will perform live at the Rosemont Theatre in Rosemont, Illinois, on Friday, November 6, 2026.
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Swerv & Friends Part 2: G Herbo, Yung Miami, Young Thug & GloRilla
Swerv & Friends Part 2 is taking over the United Center in Chicago, Illinois .
Price: see link
Los Gemelos de Sinaloa – Chicago, IL – The Gemeliza Tour
Los Gemelos de Sinaloa are bringing their highly anticipated “The Gemeliza Tour” to Chicago at the historic Byline Bank Aragon Ballroom on Friday, November 6, 2026 .
Price: see link
Ify Nwadiwe at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Ify Nwadiwe has a whole lot of hyphens!
$25 – $35
3033 Feat. Devil’s Daughter
As part of iO’s historic 45th Anniversary, the cult classic ensemble, 3033, is reuniting for a one-night-only performance–featuring the incredible opening team, Devil’s Daughter.
$25
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Hitch*Cocktails
$20
Rising Stars Burlesque Revue
The Rising Stars Burlesque Revue runs regularly in Chicago, with recurring late-night Friday performances scheduled through December 11, 2026.
Price: see link
Sophomoric Songs
$20
Saturday, November 7
iO 45th Anniversary Saturday 1-Day Pass
In 1981, iO Theater started a revolution that shaped modern comedy and launched the sharpest, funniest voices in the industry.
$35
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
Zoltan Kaszas – Worldwide(ish) Tour
Zoltan Kaszas will bring his Worldwide(ish) Tour to Chicago on Saturday, November 7, 2026.
Price: see link
Ari Matti Live
Ari Matti is performing live in Chicago on Saturday, November 7, 2026, at The Vic Theatre.
Price: see link
The Apiary
$30
Reality Detox: The Improv Experience
Price: see link
Bert Kreischer – Permission To Party World Tour
Popular stand-up comedian and podcaster Bert Kreischer is bringing his shirt-off, high-energy storytelling to Chicago, Illinois, for back-to-back nights on Friday, November 6 and Saturday, November 7, 2026,…
Price: see link
Ari Matti Live!
Estonian-born comedian and Kill Tony regular Ari Matti is bringing his bold, high-energy stand-up comedy to Chicago, Illinois, on Saturday, November 7, 2026, performing at The Vic Theatre.
Price: see link
The Niceties
$33.00
Rickey Smiley: Rickey Smiley’s Karaoke Night – Chicago, IL
Legendary comedian, actor, and radio personality Rickey Smiley is bringing a unique night of comedy and music to Chicago on Saturday, November 7, 2026 .
Price: see link
Pandji Pragiwaksono at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Pandji Pragiwaksono Wongsoyudo is an Indonesian stand-up comedian and entertainment innovator who…
$25 – $35
The Taming
In this hilarious, raucous, all-female “power-play” inspired by Shakespeare’s Shrew , contestant Katherine has the political aspirations to match her beauty pageant ambitions.
$20.00
3 Square Feat. D.A.R.E. Dropouts
Born out of the experimental genius of JTS Brown in 2002, 4 Square revolutionized long-form improvisation by stripping away sweep edits in favor of fluid and surreal scene transitions.
$30
Clued In
$25
Ballets Jazz Montreal: Dance Me – The Music of Leonard Cohen
Experience the company hailed for its “sexy, explosive, original” performances.
Price: see link
Adirondack Chair Circle
Price: see link
Beethoven 5 & Mao Fujita
Price: see link
73 Seconds
Price: see link
Dave Matthews Band – Chicago, IL – 2026 Fall Tour
Dave Matthews Band will perform live at the United Center in Chicago, Illinois, on Saturday, November 7, 2026.The concert is a key stop on their newly announced, highly exclusive 6-city North American Fall Tour 2026.
Price: see link
Premonitions Inc. at Kermess
Price: see link
The Best of IO
$22
Sinatra ’56 – Songs for Swingin’ Lovers
Sinatra ’56 — Songs for Swingin’ Lovers is the third chapter in a trilogy of cabaret concerts celebrating Frank Sinatra’s remarkable Capitol-era comeback—and the moment he hit his full, swaggering stride.
$36.57
Vladimir
Price: see link
Year One
$25
KING HEDLEY II
$40.00
Chicago Repertory Ballet: The Capulets
Price: see link
Peter Pan
$5 – $30
Jerker, or The Helping Hand
$30.00
The Snow Queen
$25.00
Rawayana – ¿Dónde es el after? World Tour
Rawayana is scheduled to perform in Chicago on Saturday, November 7, 2026, as part of their “¿Dónde es el after?
Price: see link
Jodeci – 35th Anniversary Tour of Forever My Lady
Legendary R&B group Jodeci will perform live in Chicago on Saturday, November 7, 2026, at 8:00 PM.
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Sophomoric Songs
$20
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
D.A.R.E Dropouts
$18
3 Square Feat. BL!MP
Born out of the experimental genius of JTS Brown in 2002, 4 Square revolutionized long-form improvisation by stripping away sweep edits in favor of fluid and surreal scene transitions.
$30
Top Shelf Comedy
Top Shelf Comedy is all in the name! Join us every first Saturday of the month for an incredible night of laughs!
Price: see link
Top Shelf Comedy
Top Shelf Comedy is all in the name! Join us every first Saturday of the month for an incredible night of laughs!
Price: see link
Sunday, November 8
Premonitions Inc. at Kermess
Price: see link
Ron White Live!
Ron White is performing live in Chicago on Sunday, November 8, 2026, at The Chicago Theatre.
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Joy Oladokun – Chicago – The Heavy Things Tour
Acclaimed folk-pop singer-songwriter Joy Oladokun will perform live in Chicago on Sunday, November 8, 2026, at 7:00 PM.
Price: see link
Harold Night
$15
Better Than Ezra – Chicago, IL – Live a Little Tour
90s alternative rock mainstays Better Than Ezra are bringing their signature high-energy show to Chicago, Illinois, on November 8, 2026, performing at House Of Blues.
Price: see link
Deep Schwa
$15
Barry Brewer at The Comedy Bar
Join Comedian Barry Brewer for a fun night of stand up comedy with a mix of crowd collaboration and conversation.
$30 – $40
Monday, November 9
The Armando Diaz
$17
Best of The Second City
Price: see link
Best of the Second City
Price: see link
Late Nite Mic with Vik Pandya at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring stand up comic based in Chicago.
$22 – $25
XG – XG WORLD TOUR: THE CORE
The global Japanese girl group XG is scheduled to perform live in Chicago, Illinois on Monday, November 9, 2026.
Price: see link
Hurricane Wisdom – Chicago, IL – Weathering The World Tour
Hurricane Wisdom is bringing his “Weathering The World Tour” to Chicago on Monday, November 9, 2026, at 8:00 PM.
Price: see link
$10 Improv Night
$10
Tuesday, November 10
Tuesday Good Show
Free
Tomato Throw Show at The Comedy Bar
Join us for the most fun interactive comedy show in Chicago, where the audience determines who’s the funniest (and the most unfunny) by throwing [fake] tomatoes at the stage!
$25 – $35
Dr. Neil deGrasse Tyson – Astronomy Bizarre Tour
Dr. Neil deGrasse Tyson is bringing his new show, “Astronomy Bizarre,” to Chicago on Tuesday, November 10, 2026.
Price: see link
Hunxho – Chicago, IL – 2Night Only Tour
The Atlanta-based rapper Hunxho is bringing his upcoming “2 Night Only” tour to Chicago on T uesday, November 10, 2026 .
Price: see link
Pandemonium, Please Hold
Price: see link
Michelle Branch – Chicago – Everywhere and Back Again Tour
Grammy Award-winning singer-songwriter Michelle Branch is bringing her “Everywhere and Back Again Tour” to Chicago, Illinois on Tuesday, November 10, 2026.
Price: see link
Comic Court: Chicago’s #1 Comedy Court Show
Order in the court! Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM.
$8
Wednesday, November 11
HACK JOB, A Comedy Show
HACK JOB COMEDY A biweekly showcase of Chicago’s best comedians at Blind Barber in Fulton Market!
$10
Make Believe: The Material Culture of Imaginal Religions
Join us for a pop-up gallery exhibition and book launch of Tony Wolf’s Make Believe project, a collection of assemblage artworks representing the shrines, altars and other artefacts of nine fictional religions.
Free
Two Idiot Girls LIVE
The unfiltered sister duo Drew and Deison Afualo are bringing their popular comedy podcast tour, Two Idiot Girls LIVE , to Chicago on Wednesday, November 11, 2026, at 7:00 PM .
Price: see link
Chicago’s Best Comedy Show at The Comedy Bar
Join Chicago’s best comedians for a hilarious night of stand-up comedy, pizza, and nonstop laughs!
$25 – $35
Drunk Christmas Carol
Step into Drunk Shakespeare Chicago as Dickens gets a boozy holiday shake-up
$49.00
Adirondack Chair Circle
Price: see link
Shyne & Lil Cease – Chicago – 2622 LGND Tour
Hip-hop icons Shyne and Lil Cease will perform live in Chicago on Wednesday, November 11, 2026, at 7:30 PM.
Price: see link
Play Time
$18
Peter Pan
$5 – $30
Pandemonium, Please Hold
Price: see link
Hooch & Holler Comedy Show
Price: see link
The Orbit
$15
The Fizz Show
$15
The Fizz Show
$15
Thursday, November 12
VOILÀ – Moonbloom Tour
VOILÀ is performing live in Chicago on Thursday, November 12, 2026, as a headlining stop on their “Moonbloom Tour”.
Price: see link
Fall Wine Stroll
Wine Stroll is our most popular biannual event, and a great way to support the neighborhood while tasting and discovering new wine regions and varietals.
Price: see link
American Airlines Global Wine Dinner Series: Into the Mountains: Switzerland, Austria & Hungary
City Winery presents American Airlines Global Wine Dinner Series: Into the Mountains: Switzerland, Austria & Hungary on Thursday, November 12th at 6:30 PM.
$165.00
Amber Autry – Happy Holler Tour
Stand-up comedian Amber Autry will perform live in Chicago on Thursday, November 12, 2026, as part of her Happy Holler Tour.
Price: see link
The Apiary
$30
OhJay Lamont & Friends at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on the west side of Chicago, started doing stand-up comedy in 2015.
$22 – $25
Adirondack Chair Circle
Price: see link
2021
Price: see link
Dr. Neil deGrasse Tyson – Astronomy Bizarre Tour
Dr. Neil deGrasse Tyson is bringing his new show, “Astronomy Bizarre,” to Chicago on Thursday, November 12, 2026.
Price: see link
Improv The Play
$20
Vladimir
Price: see link
Year One
$25
The Snow Queen
$25.00
Donnell Rawlings – Chicago, IL – Black & Mild Tour
Comedian, actor, and Chappelle’s Show icon Donnell Rawlings will be bringing his live stand-up tour to Chicago on Nov.
Price: see link
Charles Wesley Godwin – The Christian Name Tour
Charles Wesley Godwin is performing live in Chicago on Thursday, November 12, 2026, as part of “The Christian Name Tour”.
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Sophomoric Songs
$20
Sketch Playlist
Price: see link
Blueprint
$13
Friday, November 13
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
Nikki Glaser – The Stunning Tour
Comedian Nikki Glaser is scheduled to perform two shows in Chicago in late 2026 as part of her “The Stunning Tour”.
Price: see link
Amber Autry – Happy Holler Tour
Amber Autry will bring her Happy Holler Tour to Chicago for two back-to-back comedy sets on Friday, November 13, 2026.
Price: see link
Almost Monday – Thank God It’s Almost Monday Tour
Almost Monday will perform live at the House of Blues Chicago on Friday, November 13, 2026, at 7:00 PM.
Price: see link
The Apiary
$30
Reality Detox: The Improv Experience
Price: see link
Constellations
$35.00
Andy Haynes at The Comedy Bar
Andy Haynes is a writer, stand up and actor from Seattle, WA.
$25 – $35
Devil’s Daughter
$22
Adirondack Chair Circle
Price: see link
Andrew Bird & the CSO
Grammy-nominated violinist, songwriter and multi-instrumentalist Andrew Bird makes his CSO debut celebrating the 20-year anniversary of his acclaimed record The Mysterious Production of Eggs .
Price: see link
2021
Price: see link
She Loves Me
Price: see link
Premonitions Inc. at Kermess
Price: see link
Devil’s Daughter
$22
Vladimir
Price: see link
Year One
$25
KING HEDLEY II
$40.00
The Snow Queen
$25.00
Herman Rice & Aaron Branch – Chicago, IL – Dysfunctional Friends Tour
Comedians Herman Wrice and Aaron Branch are bringing their co-headlining tour, Dysfunctional Friends, to Chicago on Friday, November 13, 2026, at 7:30 PM .
Price: see link
Fall Series | Hubbard Street Dance Chicago
Price: see link
Devil’s Daughter
$20
Palace – USA & Canada Tour 2026
The band Palace is performing in Chicago on Friday, November 13, 2026, as part of their USA & Canada Tour 2026.
Price: see link
Cash Money & No Limit Tour: Master P, Birdman, Juvenile & Mannie Fresh
The Cash Money & No Limit Tour is coming to Chicago on Friday, November 13, 2026.
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Sophomoric Songs
$20
Andy Haynes at The Comedy Bar
Andy Haynes is a writer, stand up and actor from Seattle, WA.
$25 – $35
Wine Down Comedy
Wine Down Comedy at iO Theater invites you to relax into the weekend with great wine and Chicago’s best stand up comedians.
$45
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Hitch*Cocktails
$20
Rising Stars Burlesque Revue
The Rising Stars Burlesque Revue runs regularly in Chicago, with recurring late-night Friday performances scheduled through December 11, 2026.
Price: see link
Saturday, November 14
Pandemonium, Please Hold
Price: see link
Lucky Boys Confusion – Chicago, IL – Throwing the Game 25th Anniversary
Lucky Boys Confusion will perform a special hometown concert at the House of Blues Chicago on Saturday, November 14, 2026.
Price: see link
The Infinite Wrench
Price: see link
Nikki Glaser – The Stunning Tour
Comedian Nikki Glaser is scheduled to perform two shows in Chicago in late 2026 as part of her “The Stunning Tour”.
Price: see link
Michelle Wolf – Best Job in the World Tour
Michelle Wolf will perform her Best Job in the World stand-up tour live in Chicago on Saturday, November 14, 2026.
Price: see link
Ali Siddiq – The Custom Fit Tour
Ali Siddiq is performing live in Chicago on Saturday, November 14, 2026, at the Wintrust Arena.
Price: see link
The Apiary
$30
Reality Detox: The Improv Experience
Price: see link
The Niceties
$33.00
Andy Haynes at The Comedy Bar
Andy Haynes is a writer, stand up and actor from Seattle, WA.
$25 – $35
Clued In
$25
Grateful Shred – Fall 2026 Tour
Grateful Shred is scheduled to perform in Chicago on Saturday, November 14, 2026, at Park West.
Price: see link
Julia Jacklin: 2026 North American Tour
Julia Jacklin is performing live in Chicago on Saturday, November 14, 2026, as a major stop on her newly announced North American fall tour.
Price: see link
Sol Invictus Hervé Koubi
Led by the imaginative choreographer Hervé Koubi, Compagnie Hervé Koubi makes its Chicago premiere with the mesmerizingly kinetic Sol Invictus .
Price: see link
Adirondack Chair Circle
Price: see link
2021
Price: see link
She Loves Me
Price: see link
Premonitions Inc. at Kermess
Price: see link
The Best of IO
$22
Vladimir
Price: see link
Year One
$25
KING HEDLEY II
$40.00
The Snow Queen
$25.00
Fall Series | Hubbard Street Dance Chicago
Price: see link
Best of the Second City
Price: see link
The Cosmic Underground Show
$35 – $45
Sophomoric Songs
$20
Andy Haynes at The Comedy Bar
Andy Haynes is a writer, stand up and actor from Seattle, WA.
$25 – $35
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
D.A.R.E Dropouts
$18
Sunday, November 15
Premonitions Inc. at Kermess
Price: see link
Nikki Glaser – The Stunning Tour
Comedian Nikki Glaser is scheduled to perform three shows in Chicago in late 2026 as part of her “The Stunning Tour”.
Price: see link
SAOSIN – 20th Anniversary Tour
SAOSIN is performing at the House of Blues Chicago on Sunday, November 15, 2026, to celebrate the 20th anniversary of their iconic self-titled debut album.
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Hamilton Leithauser & Rostam – Chicago, IL – I Had a Dream That You Were Mine 10th Anniversary Tour
Indie rock heavyweights Hamilton Leithauser & Rostam will reunite for a special anniversary tour stop in Chicago on Thursday, November 12, 2026 .
Price: see link
UFO Case Files
$20
Lightly Toasted Standup Showcase
Lightly Toasted is a standup showcase at The Home Comedy Theater in the Lakeview neighborhood of Chicago every third Sunday of the month featuring up and coming and old school Chicago-based comics.
Free
Harold Night
$15
Pimpinela – Rosemont, IL – Leyendas U.S. Tour
The legendary Argentine romantic pop duo Pimpinela is performing live in Rosemont, Illinois on Sunday, November 15, 2026.
Price: see link
Deep Schwa
$15
Pimpinela – Rosemont, IL – Leyendas Tour
The iconic Argentine romantic pop duo Pimpinela is bringing their “Leyendas Tour” to Rosemont, IL on Sunday, November 15, 2026.
Price: see link
Monday, November 16
The Armando Diaz
$17
Best of The Second City
Price: see link
Best of the Second City
Price: see link
Constellations
$35.00
KING HEDLEY II
$40.00
Jessie Reyez – Chicago, IL – A Little Vengeance Tour
Jessie Reyez is bringing her massive A Little Vengeance Tour to Chicago for a live headline performance at the Byline Bank Aragon Ballroom on Monday, November 16, 2026.
Price: see link
$10 Improv Night
$10
Tuesday, November 17
Tuesday Good Show
Free
Adirondack Chair Circle
Price: see link
Don’t Worry with Phoebe Judge
Phoebe Judge , the host and co-creator of the chart-topping true-crime podcast Criminal , is kicking off her new 13-city North American live tour, “Don’t Worry,” right in her hometown of Chicago.
Price: see link
Pandemonium, Please Hold
Price: see link
Prateek Kuhad – Chicago, IL – Full Moon Chamber Tour
Acclaimed indie-folk singer-songwriter Prateek Kuhad is performing live in Chicago, IL on Tuesday, November 17, 2026.
Price: see link
Wednesday, November 18
Hawthorne Heights – Chicago – 20th Anniversary of If Only You Were Lonely Tour
Emo pioneers Hawthorne Heights are bringing their 20th Anniversary of If Only You Were Lonely Tour to Chicago on Wednesday, November 18, 2026.
Price: see link
RAD. a fun show.
A RAD alt comedy show, featuring standup, music, sketch, clown, drag, and WEIRD SH*T.
Free
Victoria Monét – Chicago, IL – Frequency of Love Tour
Grammy-winning R&B singer-songwriter Victoria Monét is bringing her “Frequency of Love Tour” to Chicago, IL on Wednesday, November 18, 2026.
Price: see link
The Neighbourhood – The World Tour 2026
The Neighbourhood is bringing “THE WOURLD TOUR” to the United Center on Wednesday, November 18, 2026.
Price: see link
Play Time
$18
tripleS – Chicago, IL – 2026 Tour
South Korean decentralized K-pop girl group tripleS will bring their spectacular 24-member live experience to Chicago on Wednesday, November 18, 2026 .
Price: see link
Pandemonium, Please Hold
Price: see link
Hooch & Holler Comedy Show
Price: see link
The Orbit
$15
The Fizz Show
$15
The Fizz Show
$15
Thursday, November 19
The Apiary
$30
Constellations
$35.00
It’s a Wonderful Life: Live in Chicago!
25th anniversary of Chicago’s holiday smash hit! Filled with heartwarming storytelling, music, and some very special surprises.
Price: see link
Ina Garten – Simply Ina Book Tour
Ina Garten is scheduled to bring her “Simply Ina ” book tour to Chicago on Thursday, November 19, 2026.
Price: see link
Little Big Town – For The Art Of It Tour
Grammy-winning country quartet Little Big Town will perform live in Chicago on Thursday, November 19, 2026, at 7:30 PM at the historic The Chicago Theatre.
Price: see link
The Jayhawks – 40th-Anniversary Tour
The Jayhawks are returning to Chicago to play a live concert at the historic Riviera Theatre on Thursday, November 19, 2026.
Price: see link
Adirondack Chair Circle
Price: see link
Jaap van Zweden & Vadim Gluzman
Rachmaninov’s Second Symphony is the orchestral equivalent of a binge-watch drama, with each movement drawing you into the next, bursting with yearning, nostalgia and soaring climaxes.
Price: see link
She Loves Me
Price: see link
Wait Wait…Don’t Tell Me
Price: see link
Improv The Play
$20
Year One
$25
Jake Cornell – Chicago, IL – 2026 Comedy Tour
Jake Cornell is bringing his stand-up comedy tour to the Foundation Room at House of Blues Chicago on Thursday, November 19, 2026.
Price: see link
The Snow Queen
$25.00
Wood Harris in Cinema & Music!
City Winery Chicago & Colossus Presents Wood Harris in Cinema & Music!
$42.00
Fall Series | Hubbard Street Dance Chicago
Price: see link
Pandemonium, Please Hold
Price: see link
Reality Detox: The Improv Experience
Price: see link
Charlie Zaa – Chicago, IL – Nacer de Nuevo Tour
Renowned Colombian romantic balladeer and bolero artist Charlie Zaa is performing live in Chicago, IL on Thursday, November 19, 2026.
Price: see link
Sketch Playlist
Price: see link
Blueprint
$13
Friday, November 20
3rd Fridays Free Admission Night
Free Admission Museum Nights take place every third Friday of each month from 5 pm to 8 pm!
Free
Beartooth – Pure Ecstasy World Tour
The heavy hitting metalcore band Beartooth is scheduled to perform live in Chicago, Illinois on Friday, November 20, 2026, as part of the newly announced U.S.
Price: see link
Pandemonium, Please Hold
Price: see link
The Infinite Wrench
Price: see link
Zhou B Art Center 3rd Friday
Zhou B Art Center opens exhibitions every 3rd Friday of the month with an evening reception from 7pm-10pm hosted by resident artists and galleries.
Free
Third Friday at Zhou B Art Center
Explore our building. Chat with the artists. Let your curiosity set the pace.
Free
Marc Maron – Yammering into the Void Tour
Marc Maron is bringing his “Yammering into the Void Tour” to the Vic Theatre in Chicago on Friday, November 20, 2026.
Price: see link
The Apiary
$30
Reality Detox: The Improv Experience
Price: see link
Best of The Second City
Price: see link
Romeo & Juliet
The Olde School Shakespeare Collective presents ROMEO & JULIET The Olde School Shakespeare Collective is bringing Shakespeare’s most famous pair of star-crossed lovers to Chicago for three performances this fall.
$20
Constellations
$35.00
Devil’s Daughter
$22
Nurse John – Against Medical Advice Tour
Nurse John is bringing his “Against Medical Advice Tour” to The Chicago Theatre on Friday, November 20, 2026.
Price: see link
Adirondack Chair Circle
Price: see link
Jaap van Zweden & Vadim Gluzman
Rachmaninov’s Second Symphony is the orchestral equivalent of a binge-watch drama, with each movement drawing you into the next, bursting with yearning, nostalgia and soaring climaxes.
Price: see link
She Loves Me
Price: see link
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