FreakShow & Tell
Aug29
Theatre & Performing Arts

FreakShow & Tell

21+ ONLY Brianna Wellen, Chicago Reader: Sideshow entertainer Thom Britton’s solo show is part performance, part demonstration. Britton is a charismatic performer who appears genuinely…

Saturday, August 29th
7:00 p.m.8:30 p.m.
Stars & Garters Theater
3914 N. Clark St.
Baby Wants Candy! The Original Completely Improvised Musical
Aug29
Music & 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…

Saturday, August 29th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Aug29
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 29th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Aug29
Theatre & Performing Arts

Redtwist Theatre’s “‘Night Mother” By Marsha Norman

Award-winning Redtwist Theatre announces the cast and creative team for ‘night Mother, April 16 – May 24, by Marsha Norman and directed by Executive Artistic…

Saturday, August 29th
7:30 p.m.9:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
The Metal Shop Performance Lab & JunkHeart Present “Anatomy of a Suicide”
Aug29
Theatre & Performing Arts

The Metal Shop Performance Lab & JunkHeart Present “Anatomy of a Suicide”

Produced in partnership with JunkHeart, The Metal Shop Performance Lab is proud to present Anatomy of a Suicide, August 12 – 30, at Redtwist Theatre,…

Saturday, August 29th
7:30 p.m.10:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Music Theater Works Presents the Beloved Classic “West Side Story”
Aug29
Theatre & Performing Arts

Music Theater Works Presents the Beloved Classic “West Side Story”

Music Theater Works is proud to announce the cast and creative team for the second production of its 2026 season, West Side Story, in the…

Saturday, August 29th
7:30 p.m.10:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
The Lincoln Lodge
Aug29
Theatre & Performing Arts

The Lincoln Lodge

The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…

Saturday, August 29th
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Best of The Second City: Chicago-Style
Aug29
Music & Comedy, Theatre & Performing Arts

Best of The Second City: Chicago-Style

The Best of The Second City: Chicago-Style is a fast-paced sketch and improv comedy revue from The Second City featuring classic scenes from its legendary…

Saturday, August 29th
8:00 p.m.9:30 p.m.
The Second City
1616 N. Wells St.
Babes With Blades Theatre Company Presents World Premiere of “yo ho.”
Aug29
Theatre & Performing Arts

Babes With Blades Theatre Company Presents World Premiere of “yo ho.”

Babes With Blades Theatre Company’s (BWBTC) 2026 season opens with a world premiere, yo ho., by playwright SMJ, directed by JD Caudill and fight choreography…

Saturday, August 29th
8:00 p.m.10:00 p.m.
The Edge Off Broadway Theatre
1133 W Catalpa Ave.
Best Of Annoyance Sketch
Aug29
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 29th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Theater of the Mind
Aug30
Theatre & Performing Arts

Theater of the Mind

Now through July 12, 2026 Multiple experiences per day at the Reid Murdoch Building, 333 N LaSalle Visit TheateroftheMindChicago.com for dates, times, and tickets Created…

Sunday, August 30th
Reid Murdoch Building – 333 N LaSalle
333 N LaSalle
The 8th Dwarf
Aug30
Theatre & Performing Arts

The 8th Dwarf

Binkley, an outsider dwarf from the Kingdom of Magical Land, is quiet, timid and scared of the dark — not exactly the best characteristics for…

Sunday, August 30th
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Music Theater Works Presents the Beloved Classic “West Side Story”
Aug30
Theatre & Performing Arts

Music Theater Works Presents the Beloved Classic “West Side Story”

Music Theater Works is proud to announce the cast and creative team for the second production of its 2026 season, West Side Story, in the…

Sunday, August 30th
2:00 p.m.5:00 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Best of The Second City
Aug30
Music & Comedy, Theatre & Performing Arts

Best of The Second City

Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…

Sunday, August 30th
3:30 p.m.5:00 p.m.
The Second City
1616 N. Wells St.
The Metal Shop Performance Lab & JunkHeart Present “Anatomy of a Suicide”
Aug30
Theatre & Performing Arts

The Metal Shop Performance Lab & JunkHeart Present “Anatomy of a Suicide”

Produced in partnership with JunkHeart, The Metal Shop Performance Lab is proud to present Anatomy of a Suicide, August 12 – 30, at Redtwist Theatre,…

Sunday, August 30th
3:30 p.m.6:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Best of The Second City
Aug31
Music & Comedy, Theatre & Performing Arts

Best of The Second City

Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…

Monday, August 31st
7:00 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
HACK JOB, A Comedy Show
Sep2
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

HACK JOB, A Comedy Show

HACK JOB COMEDY A biweekly showcase of Chicago’s best comedians at Blind Barber in Fulton Market! SHOW DETAILS: Doors @ 6 pm Show @ 7…

Wednesday, September 2nd
6:00 p.m.8:30 p.m.
Blind Barber
948 W Fulton Market
The Orbit
Sep2
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Wednesday, September 2nd
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Hooch & Holler Comedy Show
Sep2
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, September 2nd
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Sep2
Music & Comedy, Theatre & Performing Arts

The Fizz Show

Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…

Wednesday, September 2nd
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Best of The Second City: Chicago-Style
Sep3
Music & Comedy, Theatre & Performing Arts

Best of The Second City: Chicago-Style

The Best of The Second City: Chicago-Style is a fast-paced sketch and improv comedy revue from The Second City featuring classic scenes from its legendary…

Thursday, September 3rd
7:00 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Stars & Garters Presents “Stars & Garters After Dark”
Sep3
Theatre & Performing Arts

Stars & Garters Presents “Stars & Garters After Dark”

Chicago’s brand new Stars & Garters, 3914 N Clark St, presents Stars & Garters After Dark, every Thursday at 7 p.m. in the Rouge Room.…

Thursday, September 3rd
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Sep3
Theatre & Performing Arts

Redtwist Theatre’s “‘Night Mother” By Marsha Norman

Award-winning Redtwist Theatre announces the cast and creative team for ‘night Mother, April 16 – May 24, by Marsha Norman and directed by Executive Artistic…

Thursday, September 3rd
7:30 p.m.9:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Comedy Hour at Annoyance Theatre
Sep4
Sep5
Theatre & Performing Arts

Comedy Hour at Annoyance Theatre

Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…

Friday, September 4th
12:00 a.m.Saturday, September 5th
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.