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Upcoming Chicago Events

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Here 4 A Bit *Naughty Improv
May3
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, May 3rd
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Gl
May3
Festivals, Fairs & Special Events, Music & Comedy

Gl

>Presented by  United By Comedy Join us for a night of comedy with stand-up comedian Glenn Raymond, who is a throwback to legends Lenny Bruce…

Saturday, May 3rd
9:00 p.m.10:00 p.m.
The Den Theatre
1331 N Milwaukee Ave
Best Of Annoyance Sketch
May3
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 3rd
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
May3
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, May 3rd
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
May4
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 4th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wolff’s Flea Market Opening Day
May4
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, May 4th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
The Indoor Farmers Market at Water Tower Place
May4
Festivals, Fairs & Special Events

The Indoor Farmers Market at Water Tower Place

Date/Time: Sundays, 12pm – 4pm, from January 12th through Sunday, March 30th Location: Water Tower Place (835 N. Michigan Ave), Level 4 Description: Chicago’s Water Tower Place has…

Sunday, May 4th
12:00 p.m.4:00 p.m.
Water Tower Place
821 N. Michigan Ave.
South Asian Music Ensemble
May4
Music & Comedy

South Asian Music Ensemble

The South Asian Music Ensemble’s spring concert showcases the entire ensemble, featuring instrumentalists, singers, and dancers. The program highlights South Asian raga-based music with themes…

Sunday, May 4th
3:00 p.m.
Logan Center for the Arts – Penthouse, 901
915 E 60th St
Black Oak Ensemble
May4
Music & Comedy

Black Oak Ensemble

About the Performance A kaleidoscopic string trio that “fully inhabits the spirit of the works they are playing in the moment, with as ardent a…

Sunday, May 4th
3:00 p.m.5:00 p.m.
Ravinia Festival
418 Sheridan Road
For the Record | NoMI Lounge
May4
Festivals, Fairs & Special Events

For the Record | NoMI Lounge

FOR THE RECORD AT NoMI LOUNGE Every Sunday from April 6 – May 11 | 5:00 PM – 9:00 PM Reserve Now Ease into Sunday…

Sunday, May 4th
5:00 p.m.9:00 p.m.
NoMI Lounge
800 N. Michigan Ave
Keon Polee at The Comedy Bar
May4
Music & Comedy

Keon Polee at The Comedy Bar

Keon Polee is the missing link to comedy, acting, and writing. Keon Polee is from the Bay area. In 2023, Keon broke out with a…

Sunday, May 4th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
October London & Tamar Braxton – The October Nights Tour: Calling All Lovers
May4
Music & Comedy

October London & Tamar Braxton – The October Nights Tour: Calling All Lovers

October London & Tamar Braxton will perform live at The Chicago Theatre on May 4, 2025.

Sunday, May 4th
7:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
“PAWS on the Plaza” at The Langham, Chicago
May5
Festivals, Fairs & Special Events

“PAWS on the Plaza” at The Langham, Chicago

To celebrate National Pet Week, The Langham, Chicago is partnering with PAWS Chicago for a heartwarming “PAWS on the Plaza” event on Monday, May 5.…

Monday, May 5th
4:30 p.m.6:30 p.m.
Outdoor Plaza at The Langham, Chicago
330 N Wabash Ave
Tuesday Good Show
May6
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 6th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Peter Pan at Chicago Kids Company
May7
Music & Comedy

Peter Pan at Chicago Kids Company

Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…

Wednesday, May 7th
10:30 a.m.11:30 a.m.
Morgan Park Academy
2153 W 111th Street
Dame Myra Hess Memorial Concerts | Ziggy and Miles, Guitar Duo
May7
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Dame Myra Hess Memorial Concerts | Ziggy and Miles, Guitar Duo

DAME MYRA HESS MEMORIAL CONCERTS | ZIGGY AND MILES, GUITAR DUO   Program César Franck – Prélude, Fugue et Variation, op.18 Nigel Westlake – Mosstrooper…

Wednesday, May 7th
12:15 p.m.1:00 p.m.
Seventeenth Church of Christ, Scientist, Chicago
55 E. Wacker Drive
Hooch & Holler Comedy Show
May7
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 7th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Peter Pan at Chicago Kids Company
May8
Music & Comedy

Peter Pan at Chicago Kids Company

Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…

Thursday, May 8th
10:30 a.m.11:30 a.m.
Morgan Park Academy
2153 W 111th Street
2025 Lincoln Park Uncorked: An Armitage – Halsted Wine Stroll
May8
Festivals, Fairs & Special Events

2025 Lincoln Park Uncorked: An Armitage – Halsted Wine Stroll

2025 Lincoln Park Uncorked: An Armitage – Halsted Wine Stroll Toast the spring at Lincoln Park Uncorked: An Armitage – Halsted Wine Stroll! Buy your…

Thursday, May 8th
6:00 p.m.9:00 p.m.
Wintrust Bank – Lincoln Park
935 W. Armitage
Teatro Zinzanni
May8
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…

Thursday, May 8th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Attack On Titan: Beyond The Walls World Tour – The Official Concert
May8
Music & Comedy

Attack On Titan: Beyond The Walls World Tour – The Official Concert

Featuring the internationally acclaimed soundtrack composed by Hiroyuki SAWANO (Seasons 1, 2, 3 and The Final Season) and KOHTA YAMAMOTO (The Final Season), the concert…

Thursday, May 8th
7:30 p.m.9:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Secret Family
May8
Music & Comedy

Secret Family

Secret Family is a sketch comedy group that’s exactly like a real family, only our drama and infighting is mostly pretend, and our love for…

Thursday, May 8th
8:00 p.m.9:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Peter Pan at Chicago Kids Company
May9
Music & Comedy

Peter Pan at Chicago Kids Company

Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…

Friday, May 9th
10:30 a.m.11:30 a.m.
Morgan Park Academy
2153 W 111th Street
SAUCED Spring Night Market
May9
Festivals, Fairs & Special Events

SAUCED Spring Night Market

How do you support small businesses? At a time when the economy is in chaos, this question is more important than ever. At SAUCED, the…

Friday, May 9th
5:00 p.m.10:00 p.m.
Half Acre Beer Co
2050 W Balmoral Ave
bean-night

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