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The Smiley Tilmon Blues Band featuring Kate Moss
May11
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

The Smiley Tilmon Blues Band featuring Kate Moss

The Smiley Tilmon Band, featuring Kate Moss, performs at The Tonk Live on Saturday, May 11th, from 8 to 11 p.m. Smiley Tilmon, an 84-year-old…

Saturday, May 11th
8:00 p.m.11:00 p.m.
The Tonk
1800 S Racine Ave
Best Of Annoyance Sketch
May11
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, May 11th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Muse: Earth
May11
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Muse: Earth

Muse is a live music experience that incorporates drag, burlesque, clowning and other art forms to explore universal themes. Muse: Earth is the final installment…

Saturday, May 11th
9:30 p.m.11:00 p.m.
Newport Theatre
956 W Newport Ave
Teatro Zinzanni
May12
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, May 12th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
FREE Concert Featuring Très Belle & Paul Dykstra
May12
Music & Comedy, Theatre & Performing Arts

FREE Concert Featuring Très Belle & Paul Dykstra

Enjoy a free concert featuring the soprano trio Très Belle accompanied by pianist Paul Dykstra, as part of a special Mother’s Day concert at Concordia…

Sunday, May 12th
12:00 p.m.1:00 p.m.
Concordia Lutheran Church
3855 N. Seeley Ave
Swingin’ on a Star
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Swingin’ on a Star

Join us for a lovely Mother’s Day Brunch. The fabulous harmonies of the Swingin’ Sisters will charm and uplift your spirits as we swing into…

Sunday, May 12th
12:00 p.m.1:30 p.m.
Le Piano
6970 N. Glenwood Ave.
University Wind Ensemble
May12
Music & Comedy

University Wind Ensemble

The University Wind Ensemble is joined by special guest artists for two captivating works: Alan Theisen’s AMP concerto for piano and wind ensemble featuring pianist Marianne Parker,…

Sunday, May 12th
2:00 p.m.
Logan Center for the Arts – Performance Hall
915 E 60th St
Early Music Ensemble
May12
Music & Comedy

Early Music Ensemble

The Early Music Ensemble completes its year-long commemoration of the life of William Byrd with a performance of the complete Mass for Five Voices. The…

Sunday, May 12th
5:00 p.m.
Logan Center for the Arts – Penthouse, 901
915 E 60th St
Miz Cracker – Big Gay Cabaret
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Miz Cracker – Big Gay Cabaret

Miz Cracker is a New York City drag queen—and a writer, foodie, and comedienne. She launched her drag career in 2011 while participating in marches…

Sunday, May 12th
5:00 p.m.6:00 p.m.
Venus Cabaret Theater
3741 North Southport Avenue
Mother’s Day Celebration: Yolanda Adams, Fred Hammond & Tamela Mann
May12
Music & Comedy

Mother’s Day Celebration: Yolanda Adams, Fred Hammond & Tamela Mann

Treat The Mother In Your Life To A Mother’s Day Celebration featuring gospel’s biggest artists and new trailblazers that you must see. This Show Features…

Sunday, May 12th
6:00 p.m.10:00 p.m.
House Of Hope
752 E 114th St
Da Wittle Team Show
May12
Music & Comedy

Da Wittle Team Show

Da Wittle Team Show is an improv showcase spotlighting some of the best small-prov teams in the city. Each week, a different lineup of hot, diverse…

Sunday, May 12th
7:00 p.m.8:00 p.m.
iO Theater
1501 N. Kingsbury St.
Craig Pomranz: Berlin to Dylan to Simon & Garfunkel
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Craig Pomranz: Berlin to Dylan to Simon & Garfunkel

Craig Pomranz returns to Chicago with his show Berlin to Dylan to Simon & Garfunkel: Songbook throughout the years. Critics rave “Best Male Vocalist!”,  “Tenor…

Sunday, May 12th
7:00 p.m.8:30 p.m.
Davenport’s Piano Bar and Cabaret
1383 North Milwaukee Avenue
University Chorus
May13
Music & Comedy

University Chorus

Enjoy classical repertoire from different periods, songs from around the world, and a performance of Freedom Land, a Gullah stickpounding choral collaboration led by Visiting Artist-in-Residence…

Monday, May 13th
7:30 p.m.
Logan Center for the Arts – Performance Hall
915 E 60th St
Studs’ Place – One more time (Musical Mondays)
May13
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Studs’ Place – One more time (Musical Mondays)

A musical salute to Chicago’s own Studs Terkel by Chicago Cabaret Professionals. Studs Terkel, the great writer/interviewer, produced essays and conversations on almost every genre…

Monday, May 13th
7:30 p.m.9:30 p.m.
The Rhapsody Theater
1328 W Morse Ave
Music beyond cultural divides: Celebrating 30 years of sister city friendship: Chicago & Hamburg
May13
Music & Comedy

Music beyond cultural divides: Celebrating 30 years of sister city friendship: Chicago & Hamburg

The Hamburg Committee of the Chicago Sister Cities International (CSCI) is proud to celebrate the 30th anniversary of our sister city relationship with Hamburg in…

Monday, May 13th
8:00 p.m.9:30 p.m.
Museum of Contemporary Art
220 E. Chicago Ave.
Craig David – 7 Days Commitment Tour 2024
May13
Music & Comedy

Craig David – 7 Days Commitment Tour 2024

Legendary British singer / songwriter Craig David will perform live at The Chicago Theatre on May 13, 2024.

Monday, May 13th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
A Smashing Hot Evening with Lynne Jordan
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

A Smashing Hot Evening with Lynne Jordan

In a city brimming with classic blues and jazz divas, Lynne Jordan stands apart. Not only do her soaring vocals dip effortlessly into blues, jazz,…

Tuesday, May 14th
5:00 p.m.9:00 p.m.
The Cliff Dwellers
200 S. Michigan Ave, 22nd Fl
CSO Brass Quintet Plays Bach & More
May14
Music & Comedy, Theatre & Performing Arts

CSO Brass Quintet Plays Bach & More

Known for its ongoing legacy of excellence, the CSO Brass Quintet has been performing at near-capacity events for decades. Its mission, says quintet member and…

Tuesday, May 14th
6:30 p.m.8:00 p.m.
Chicago Symphony Center
220 S Michigan Ave
Tuesday Good Show
May14
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, May 14th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Café Carly – When I Grow Up
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Café Carly – When I Grow Up

Café Carly cabaret show — featuring Chicago’s most talented young musical theater performers, wrangled into a uniquely themed show by hometown girl (and former NYC…

Tuesday, May 14th
7:30 p.m.
Hey Nonny
10 S. Vail Ave.
Chamber Music Showcase
May14
Music & Comedy

Chamber Music Showcase

Musicians from the Chamber Music Program present an exciting evening of classical and contemporary works for small ensembles. Free admission

Tuesday, May 14th
7:30 p.m.
Fulton Recital Hall, Goodspeed Hall
1010 E. 59th St.
Chicago’s Best Standup
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Chicago’s Best Standup

Chicago’s Best Standup Comedy is back better than ever. We’ve compiled the absolute best standup comedy lineup that you will see in the city. Today’s…

Tuesday, May 14th
7:30 p.m.9:00 p.m.
Laugh Factory, 3175 N. Broadway St, Chicago, IL 60657
3175 N. Broadway St
Happy 2 B Here – Sketch Comedy for Everyone
May14
Music & Comedy, Theatre & Performing Arts

Happy 2 B Here – Sketch Comedy for Everyone

HAPPY 2 B HERE is a kaleidoscopic sketch comedy extravaganza starring Liz Gordon, Alba Woolard, Catrina Hughes, Willis Brei, and Conor Delaney. It’s a show…

Tuesday, May 14th
8:00 p.m.9:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Best Night Ever Comedy Show
May14
Music & Comedy, Theatre & Performing Arts

Best Night Ever Comedy Show

Best Night Ever is one of the city’s longest-running standup comedy showcases. Since 2009 the show has been highlighting comics from all over the city…

Tuesday, May 14th
8:00 p.m.10:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave
bean-night

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