John Cusack with a Screening of Grosse Pointe Blank
Jun13
Music & Comedy

John Cusack with a Screening of Grosse Pointe Blank

An Evening with John Cusack and Screening of Grosse Pointe Blank is scheduled to take place in Chicago on Saturday, June 13, 2026. The event…

Saturday, June 13th
7:30 p.m.9:30 p.m.
Auditorium
50 East Ida B. Wells Drive
Brahms Symphony No. 4
Jun13
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Brahms Symphony No. 4

Giancarlo Guerrero leads the Grant Park Orchestra in Brahms’s Symphony No. 4, the composer’s poignant final symphony. Gabriela Lena Frank’s harrowing Conquest Requiem and Charles Ives’s eclectic Variations…

Saturday, June 13th
7:30 p.m.9:30 p.m.
Millennium Park
201 E Randolph Street
Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the Apollo Theater
Jun13
Music & Comedy, Theatre & Performing Arts

Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the Apollo Theater

Following the success of the Going Bacharach: The Songs Of An Icon Chicago debut, the musical revue has been extended to run through June 21 at the Apollo Theater. Rediscover the…

Saturday, June 13th
7:30 p.m.9:30 p.m.
Apollo Theater
2550 N. Lincoln Ave.
Secret Sketch Show
Jun13
Music & Comedy

Secret Sketch Show

Shhhhh! It’s a secret! Don’t tell anyone but your favorite iO performers are hosting a wild night of variety and sketch. Secret sketch show is…

Saturday, June 13th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Leah Lamarr at The Comedy Bar
Jun13
Music & Comedy

Leah Lamarr at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Leah Lamarr is an internationally touring…

Saturday, June 13th
9:00 p.m.10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Best Of Annoyance Sketch
Jun13
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, June 13th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
UFO Case Files
Jun14
Music & Comedy

UFO Case Files

Men in Black meets Whose Line Is It Anyways? UFO Case Files is a live improv show in Logan Square where the cast creates a…

Sunday, June 14th
7:00 p.m.8:00 p.m.
cosmic underground theater
3433 W Fullerton Ave
Gerard Michaels at The Comedy Bar
Jun14
Music & Comedy

Gerard Michaels at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry A co-star of Antonio Banderas in…

Sunday, June 14th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Pour Minds Podcast – Still Sippin’ Tour
Jun14
Music & Comedy

Pour Minds Podcast – Still Sippin’ Tour

The Pour Minds Podcast, hosted by Drea and Mia, is bringing the Still Sippin’ Tour to Chicago on Sunday, June 14, 2026.

Sunday, June 14th
7:00 p.m.9:00 p.m.
Park West
322 W Armitage Ave
Amyl and The Sniffers: North American 2026 Tour
Jun14
Music & Comedy

Amyl and The Sniffers: North American 2026 Tour

Australian punk rock firebrands Amyl and The Sniffers /w special guests Party Dozen and L7 will perform live at Chicago’s The Salt Shed Outdoors on…

Sunday, June 14th
7:00 p.m.10:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Stand By Me: The Film and Its Stars 40 Years Later
Jun14
Music & Comedy

Stand By Me: The Film and Its Stars 40 Years Later

To celebrate the 40th anniversary of the classic coming-of-age film, the special event “Stand By Me: The Film and Its Stars 40 Years Later” is…

Sunday, June 14th
7:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Wheel of Improv
Jun14
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, June 14th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the Apollo Theater
Jun14
Music & Comedy, Theatre & Performing Arts

Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the Apollo Theater

Following the success of the Going Bacharach: The Songs Of An Icon Chicago debut, the musical revue has been extended to run through June 21 at the Apollo Theater. Rediscover the…

Sunday, June 14th
7:30 p.m.9:30 p.m.
Apollo Theater
2550 N. Lincoln Ave.
Millennium Park Summer Music Series
Jun15
Music & Comedy

Millennium Park Summer Music Series

Featuring: Arrested Development Linda Sol DJ Ca$h Era Millennium Park Summer Music Series features a wide variety of music from established and emerging artists at…

Monday, June 15th
6:30 p.m.9:00 p.m.
Millennium Park – Jay Pritzker Pavilion
201 E Randolph St
Magic Mondays
Jun15
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday, June 15th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Late Nite Mic with Vik Pandya at The Comedy Bar
Jun15
Music & Comedy

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…

Monday, June 15th
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Michael Charles and Band on The Tall Ship Windy Music Concert Series
Jun15
Music & Comedy

Michael Charles and Band on The Tall Ship Windy Music Concert Series

We’ll help you chase your “Monday blues”, aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of…

Monday, June 15th
7:00 p.m.9:00 p.m.
Tall Ship Windy
600 East Grand Avenue Navy Pier
Del Amitri Live In Concert
Jun15
Music & Comedy

Del Amitri Live In Concert

Scottish alternative rock band Del Amitri is scheduled to perform in Chicago on Monday, June 15, 2026.

Monday, June 15th
7:30 p.m.10:30 p.m.
The Vic Theatre
3145 N. Sheffield
CSO Chamber Music: CSO Brass Quintet
Jun16
Music & Comedy

CSO Chamber Music: CSO Brass Quintet

As part of Symphony Center’s tribute to America’s 250th anniversary, the renowned CSO Brass Quintet presents a program highlighting the power and pageantry of brass…

Tuesday, June 16th
6:30 p.m.8:00 p.m.

220 S. Michigan Ave.
Tuesday Good Show
Jun16
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, June 16th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Tomato Throw Show at The Comedy Bar
Jun16
Music & Comedy

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]…

Tuesday, June 16th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Jazzin’ at the Shedd
Jun17
Museums, Galleries & Exhibitions, Music & Comedy

Jazzin’ at the Shedd

Live jazz revels at Shedd Aquarium! Join us for the popular midweek  Jazzin’ at the Shedd series with unforgettable evenings of music, mingling and marine life.…

Wednesday, June 17th
5:00 p.m.10:00 p.m.
Shedd Aquarium
1200 S. Lake Shore Dr.
Haydn Military Symphony
Jun17
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Haydn Military Symphony

Percussive bombast suggests an advancing army in Haydn’s Military Symphony No. 100 in this thrilling program conducted by Giancarlo Guerrero. After Julia Perry’s energetic Short Piece, young cello…

Wednesday, June 17th
6:30 p.m.8:00 p.m.
Millennium Park
201 E Randolph Street
Crowd Work Wednesday at The Comedy Bar
Jun17
Music & Comedy

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. Hosted by Chicago comedians Pat…

Wednesday, June 17th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611