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Upcoming Chicago Events

Check out what's happening all around Chicago.

Best Of Annoyance Sketch
Aug23
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, August 23rd
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Aug23
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, August 23rd
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Chicago’s Only Classical Music Street Festival Celebrates 10 Years
Aug24
Festivals, Fairs & Special Events, Music & Comedy

Chicago’s Only Classical Music Street Festival Celebrates 10 Years

Access Contemporary Music (ACM) proudly presents the 10th Annual Thirsty Ears Festival, Chicago’s only classical music street festival, returning August 23–24, 2025. The festival transforms Wilson Avenue into a vibrant celebration of classical…

Sunday, August 24th
ACM School of Music
1758 W. Wilson St.
Simple Plan – Bigger Than You Think! Tour
Aug24
Music & Comedy

Simple Plan – Bigger Than You Think! Tour

Pop-punk veterans Simple Plan are celebrating their 25th anniversary as a band in a big way, announcing a headlining Summer 2025 US tour with support…

Sunday, August 24th
6:30 p.m.9:30 p.m.
Alexander Nate (Live in Technicolor) at Thalia Hall
Aug24
Music & Comedy

Alexander Nate (Live in Technicolor) at Thalia Hall

With a captivating blend of soulful melodies and deeply heartfelt lyrics, Alexander Nate has carved out a distinct space for himself in the music world.…

Sunday, August 24th
6:30 p.m.9:30 p.m.
Thalia Hall
1807 South Allport Street
Jalen Hinton at The Comedy Bar
Aug24
Music & Comedy

Jalen Hinton at The Comedy Bar

Hailing from St. Louis, Missouri, Jalen Hinton (known as J.One.8) brings a fresh, family-friendly take to the comedy stage with sharp wit, relatable stories, and a knack…

Sunday, August 24th
7:00 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
The Annoyance Sketch Show: Late Stage Everything
Aug24
Music & Comedy, Theatre & Performing Arts

The Annoyance Sketch Show: Late Stage Everything

The trains are late, the apps are broken, the bees are dying, and the algorithm knows your deepest fears. So what do we do? We…

Sunday, August 24th
8:00 p.m.9:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Broadway Night at the Grant Park Music Festival
Aug25
Festivals, Fairs & Special Events, Music & Comedy, Tours & Attractions

Broadway Night at the Grant Park Music Festival

For over 90 years, the Grant Park Music Festival has offered free classical music in the heart of Chicago. This weekend, Celebrate the enduring legacy…

Monday, August 25th
6:30 p.m.10:45 p.m.
Millennium Park
201 E Randolph Street
Drunk Shakespeare!
Aug25
Music & Comedy

Drunk Shakespeare!

Gift this experience to your loved ones! Click here to check out our gift card. Join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry,…

Monday, August 25th
7:00 p.m.8:30 p.m.
The Lounge At The Lion
182 North Wabash Avenue
The Late Nite Mic at The Comedy Bar
Aug25
Music & Comedy

The Late Nite Mic 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, August 25th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Cappella Pratensis
Aug26
Music & Comedy

Cappella Pratensis

Cappella Pratensis transforms Renaissance polyphony from dusty manuscript to living sound. One of the world’s only ensembles to sing directly from historical notation, their collective…

Tuesday, August 26th
3:00 p.m.4:30 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Tuesday Good Show
Aug26
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, August 26th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Tomato Throw Show
Aug26
Music & Comedy

Tomato Throw Show

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…

Tuesday, August 26th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Tomato Throw Show at The Comedy Bar
Aug26
Music & Comedy

Tomato Throw Show at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Come hang with us at Chicago’s…

Tuesday, August 26th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Jonas Brothers – JONAS 20: Living the Dream Tour
Aug26
Music & Comedy

Jonas Brothers – JONAS 20: Living the Dream Tour

Jonas Brothers will return to Wrigley Field this summer as part of the JONAS 20: Living the Dream tour! Their performance at the Friendly Confines…

Tuesday, August 26th
7:30 p.m.10:30 p.m.
Wrigley Field
1060 West Addison Street
Comic Court: The Best Comedy Show in the World
Aug26
Music & Comedy, Theatre & Performing Arts

Comic Court: The Best Comedy Show in the World

Would you rather be able to fly or be able to turn invisible? Who are we more tired of: Ryan Reynolds or Dwayne Johnson? Would…

Tuesday, August 26th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Dame Myra Hess Memorial Concerts | Zachary Brandon, Violin and Sung Hoon Mo, Piano
Aug27
Music & Comedy, Theatre & Performing Arts

Dame Myra Hess Memorial Concerts | Zachary Brandon, Violin and Sung Hoon Mo, Piano

DAME MYRA HESS MEMORIAL CONCERTS | ZACHARY BRANDON, VIOLIN SUNG HOON MO, PIANO   Program Claude Debussy – Violin Sonata in G minor Gabriel Fauré…

Wednesday, August 27th
12:15 p.m.1:00 p.m.
Seventeenth Church of Christ, Scientist, Chicago
55 E. Wacker Drive
Michael Learns to Rock: Take Us to Your Heart Tour
Aug27
Music & Comedy

Michael Learns to Rock: Take Us to Your Heart Tour

Danish soft rock and pop rock band Michael Learns to Rock brings the Take Us To Your Heart Tour to The Chicago Theatre on August…

Wednesday, August 27th
7:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Crowd Work Wednesday
Aug27
Music & Comedy

Crowd Work Wednesday

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…

Wednesday, August 27th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Neil Young – Love Earth World Tour
Aug27
Music & Comedy

Neil Young – Love Earth World Tour

Legendary singer-songwriter Neil Young will perform live at Huntington Bank Pavilion at Northerly Island on Aug. 27, 2025.

Wednesday, August 27th
7:30 p.m.10:30 p.m.
The Annoyance Sketch Show: Late Stage Everything
Aug27
Music & Comedy, Theatre & Performing Arts

The Annoyance Sketch Show: Late Stage Everything

The trains are late, the apps are broken, the bees are dying, and the algorithm knows your deepest fears. So what do we do? We…

Wednesday, August 27th
8:00 p.m.9:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Hooch & Holler Comedy Show
Aug27
Music & Comedy, Theatre & Performing Arts

Hooch & Holler Comedy Show

Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…

Wednesday, August 27th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Teatro Zinzanni
Aug28
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Thursday, August 28th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Chris Brown: Breezy Bowl XX Platinum Tour
Aug28
Music & Comedy

Chris Brown: Breezy Bowl XX Platinum Tour

Chris Brown announced his upcoming Breezy Bowl XX tour which includes a show at Wrigley Field Thursday, August 28. The performance at the Friendly Confines…

Thursday, August 28th
6:30 p.m.10:00 p.m.
Wrigley Field
1060 West Addison Street
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