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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.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.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…
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.Huntington Bank Pavilion at Northerly Island
1300 S. Linn White Dr.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 StreetMusic & 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.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.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 StreetMusic & 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 AvenueMusic & 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…
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 StMusic & 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 AveMusic & 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…
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.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 StreetMusic & 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 AvenueMusic & 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 DriveMusic & 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. StateMusic & 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…
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.Huntington Bank Pavilion at Northerly Island
1300 S. Linn White Dr.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.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 DivisionMusic & 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. RandolphMusic & 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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