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Music & Comedy
An hour with Sabeen Sadiq
Sabeen Sadiq is back in Chicago with a brand-new hour of hilarious and deeply personal comedy. From the chaos of dating to the quiet heartbreaks…
Saturday, August 23rd
6:00 p.m. – 7:30 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueMusic & Comedy, Theatre & Performing Arts
The Dinner Detective True Crime Murder Mystery Dinner Show
The Dinner Detective is an interactive true crime mystery show set in the present day and based on real cold cases. Feast on a fantastic…
Saturday, August 23rd
6:00 p.m. – 9:00 p.m.Courtyard by Marriott Chicago Downtown
165 E. Ontario StMusic & 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…
Saturday, August 23rd
6:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphSaturday, August 23rd
6:45 p.m. – 10:00 p.m.Credit Union 1 Amphitheatre
19100 Ridgeland AveMusic & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Saturday, August 23rd
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Music & Comedy
“Something’s Stinky” with Brian Reitz & friends
Brian Reitz will be debuting his 30-minute standup special Something’s Stinky. A few funny friends will perform, too.
Saturday, August 23rd
7:00 p.m. – 8:00 p.m.The Den Theatre
1331 N Milwaukee AveMusic & Comedy
Cumbia Catedral
Get ready for an unforgettable “Cumbia Catedral” at The Epiphany in Chicago!Join us for a night of high-energy rhythms, featuring a special national live performance…
Saturday, August 23rd
7:00 p.m. – Sunday, August 24th
1:00 a.m.Epiphany Center for the Arts
201 South Ashland AvenueMusic & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Saturday, August 23rd
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy, Theatre & Performing Arts
Improvised Shakespeare
Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare
Music & Comedy
Late Night Shenanigans Presents: Full Moon, Half Brains
From Chicago to New York City Late Night Shenanigans returns to the Annoyance Theatre with a new collection of sketches that mix absurd characters, physical…
Saturday, August 23rd
8:00 p.m. – 9:00 p.m.Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.Music & Comedy, Theatre & Performing Arts
ComedySportz Chicago
Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…
Saturday, August 23rd
8:00 p.m. – 9:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
The Cosmic Underground Show
The Cosmic Underground Show is a 90-minute, fast-paced, and hilariously mind-bending experience that blends cutting-edge magic with retro-futuristic flair. Set inside the recently unearthed Cosmic…
Saturday, August 23rd
8:00 p.m. – 9:30 p.m.cosmic underground theater
3433 W Fullerton AveMusic & Comedy
Benson Boone – American Heart Tour
Benson Boone is bringing his American Heart Tour to United Center on August 23!
Saturday, August 23rd
8:00 p.m. – 11:00 p.m.United Center
1901 W Madison St.Music & Comedy, Theatre & Performing Arts
Here 4 A Bit *Naughty Improv
Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…
Saturday, August 23rd
9:00 p.m. – 10:00 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & 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.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…
Sunday, August 24th
5:00 a.m. – 9:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & 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 Avenue

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