Ruth Fuerst — Quirky (Quirky songs written by quirky songwriters sung by a quirky singer)
May17
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Ruth Fuerst — Quirky (Quirky songs written by quirky songwriters sung by a quirky singer)

Since when do irreverence and genuine warmth go together? Since “Quirky”! Come hear a mix of offbeat, funny, honest and uplifting songs about love, longing…

Sunday, May 17th
6:00 p.m.9:00 p.m.
Fulton Street Collective
1821 W Hubbard St UNIT 307
Jack Grady at The Comedy Bar
May17
Music & Comedy

Jack Grady at The Comedy Bar

Jack Grady is a comedy magician whose chaotic, unpredictable style has earned him a cult following and millions of fans across the internet. One of…

Sunday, May 17th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Wheel of Improv
May17
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, May 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Sunday Best Comedy Show In Chicago
May17
Music & Comedy

Sunday Best Comedy Show In Chicago

An affordable 90 minute showcase featuring the best of Chicago comedy on a Sunday! Join us every Sunday at 7:30 for Chicago’s BEST standup comedy show—it’s…

Sunday, May 17th
7:30 p.m.9:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Julio Torres Live
May17
Music & Comedy

Julio Torres Live

Julio Torres is scheduled to perform in Chicago on Sunday, May 17, 2026, for his “Works in Progress” show.

Sunday, May 17th
7:30 p.m.9:30 p.m.
Park West
322 W Armitage Ave
Good Kid – Can We Hang Out? 2026 Tour
May17
Music & Comedy

Good Kid – Can We Hang Out? 2026 Tour

Toronto indie rock band Good Kid /w special guest Inoha will perform live at Chicago’s Riviera Theatre on May 17, 2026.

Sunday, May 17th
7:30 p.m.10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Bruno Mars – The Romantic Tour
May17
Music & Comedy

Bruno Mars – The Romantic Tour

16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago’s Soldier Field on May 16-17, 2026.

Sunday, May 17th
7:30 p.m.11:30 p.m.
Soldier Field
1410 Special Olympics Drive
That 90s Throwback Comedy Show
May17
Music & Comedy, Theatre & Performing Arts

That 90s Throwback Comedy Show

Calling all 90s kids! This show is for you. Each month, Chicago’s hottest comedians share their favorite 90s obsessions while the audience battles over trivia…

Sunday, May 17th
8:00 p.m.9:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Magic Mondays
May18
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday, May 18th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Late Nite Mic with Vik Pandya at The Comedy Bar
May18
Music & Comedy

Late Nite Mic with Vik Pandya 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, May 18th
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Chaos and Carnage: Thy Art Is Murder, Carnifex & Bodysnatcher
May19
Music & Comedy

Chaos and Carnage: Thy Art Is Murder, Carnifex & Bodysnatcher

The Chaos and Carnage 2026 tour will be at the Ramova Theatre in Chicago on Tuesday, May 19, 2026. This year’s installment features a massive…

Tuesday, May 19th
4:45 p.m.10:00 p.m.
Ramova Theatre
3520 S. Halsted St.
Tuesday Good Show
May19
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 19th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Joe Jackson – Hope and Fury Tour
May19
Music & Comedy

Joe Jackson – Hope and Fury Tour

Joe Jackson and his band are scheduled for a two-night residency at Park West in Chicago on Tuesday, May 19, and Wednesday, May 20, 2026.…

Tuesday, May 19th
7:30 p.m.10:30 p.m.
Park West
322 W Armitage Ave
Best Night Ever
May19
Music & Comedy

Best Night Ever

Your best bet for Tuesday night laughs with one of Chicago’s most critically acclaimed comedy showcases! Every Tuesday, we will bring you the best lineup…

Tuesday, May 19th
8:00 p.m.9:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Clever Comedy Show
May19
Music & Comedy

Clever Comedy Show

A comedy showcase featuring acts ranging from the freshest comedy club killers to alt-comedy geniuses, musical acts & surprise drop-ins. Looking for a hilarious unique…

Tuesday, May 19th
9:00 p.m.10:15 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Crowd Work Wednesday at The Comedy Bar
May20
Music & Comedy

Crowd Work Wednesday at The Comedy Bar

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, May 20th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Chicago’s Late Night Talk Show: The Not That Late Show
May20
Music & Comedy

Chicago’s Late Night Talk Show: The Not That Late Show

A monthly late night style talk show featuring comedy, music and interviews with notable Chicagoans. Get the late night talk show experience without heading to…

Wednesday, May 20th
7:30 p.m.9:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Leftist political commentator Lily Eagla joins Chicago’s Late Night Talk Show
May20
Music & Comedy

Leftist political commentator Lily Eagla joins Chicago’s Late Night Talk Show

Get the late night talk show experience without heading to NYC or LA. The Not That Late Show is a POC- and queer-led late-night talk…

Wednesday, May 20th
7:30 p.m.9:00 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Khalid – It’s Always Summer Somewhere 2026 Tour
May20
Music & Comedy

Khalid – It’s Always Summer Somewhere 2026 Tour

Multi-platinum artist Khalid /w special guest Lauv will perform live at Chicago’s Huntington Bank Pavilion at Northerly Island on May 20, 2026.

Wednesday, May 20th
7:30 p.m.10:30 p.m.
Chet Faker – A Love For Strangers World Tour
May20
Music & Comedy

Chet Faker – A Love For Strangers World Tour

Chet Faker is scheduled to perform in Chicago on Wednesday, May 20, 2026, as part of his A Love For Strangers World Tour. This tour…

Wednesday, May 20th
7:30 p.m.10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Joe Jackson – Hope and Fury Tour
May20
Music & Comedy

Joe Jackson – Hope and Fury Tour

Joe Jackson and his band are scheduled for a two-night residency at Park West in Chicago on Tuesday, May 19, and Wednesday, May 20, 2026.…

Wednesday, May 20th
7:30 p.m.10:30 p.m.
Park West
322 W Armitage Ave
Hooch & Holler Comedy Show
May20
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, May 20th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
May20
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, May 20th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Morgan’s Laugh Lounge
May21
Music & Comedy

Morgan’s Laugh Lounge

Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…

Thursday, May 21st
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market