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The 26th Anniversary Englewood Jazz Festival
Sep16
Festivals, Fairs & Special Events, Music & Comedy

The 26th Anniversary Englewood Jazz Festival

The 26th Annual Englewood Jazz Festival, presented by Live the Spirit Residency, returns to Chicago’s historic Hamilton Park on September 18–20, 2025, marking a powerful…

Tuesday, September 16th
Hamilton Park and Cultural Center
513 W 72nd St
The 26th Anniversary Englewood Jazz Festival
Sep17
Festivals, Fairs & Special Events, Music & Comedy

The 26th Anniversary Englewood Jazz Festival

The 26th Annual Englewood Jazz Festival, presented by Live the Spirit Residency, returns to Chicago’s historic Hamilton Park on September 18–20, 2025, marking a powerful…

Wednesday, September 17th
Hamilton Park and Cultural Center
513 W 72nd St
Crowd Work Wednesday
Sep17
Music & Comedy

Crowd Work Wednesday

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, September 17th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
The Annoyance Sketch Show: Late Stage Everything
Sep17
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…

Wednesday, September 17th
8:00 p.m.9:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Steven Wilson – The Overview Tour
Sep17
Music & Comedy

Steven Wilson – The Overview Tour

Six-time-Grammy Award-nominated musician, songwriter and producer Steven Wilson has announced the eagerly awaited North American leg of “The Overview” tour — his first full-band solo headline run in the…

Wednesday, September 17th
8:00 p.m.11:00 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Lady Gaga – The Mayhem Ball Tour
Sep17
Music & Comedy

Lady Gaga – The Mayhem Ball Tour

After much anticipation, 14-time Grammy Award-winner Lady Gaga is heading out on ‘The MAYHEM Ball’ tour with stops at United Center on September 15 and…

Wednesday, September 17th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Alex G: 2025 North American Tour
Sep17
Wednesday, September 17th
8:00 p.m.11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Hooch & Holler Comedy Show
Sep17
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 17th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The 26th Anniversary Englewood Jazz Festival
Sep18
Festivals, Fairs & Special Events, Music & Comedy

The 26th Anniversary Englewood Jazz Festival

The 26th Annual Englewood Jazz Festival, presented by Live the Spirit Residency, returns to Chicago’s historic Hamilton Park on September 18–20, 2025, marking a powerful…

Thursday, September 18th
Hamilton Park and Cultural Center
513 W 72nd St
Teatro Zinzanni
Sep18
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, September 18th
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
YUPLUS
Sep18
Music & Comedy, Theatre & Performing Arts

YUPLUS

Come be a part of the first taping of YUPLUS, Chicago’s own live comedy game show! Three comedians represent their respective cities: New York vs.…

Thursday, September 18th
7:00 p.m.10:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Olympus Has Fallen (And It Can’t Get Up)
Sep18
Music & Comedy, Theatre & Performing Arts

Olympus Has Fallen (And It Can’t Get Up)

Olympus Has Fallen (And it Can’t Get Up) is a sketchy retelling of your favorite Greek myths. As educational as it is explicit, this hour-long…

Thursday, September 18th
7:30 p.m.8:30 p.m.
The De Matt Theater at The Second City
230 W North Ave
Magically Ever After: An Evening with The Cosmic Romantics
Sep18
Music & Comedy, Theatre & Performing Arts

Magically Ever After: An Evening with The Cosmic Romantics

A vaudeville-inspired magic show that blends dazzling sleight of hand with comedy, music, and heartfelt storytelling, starring real life couple Elizabeth Messick & Eric Thirstin,…

Thursday, September 18th
7:30 p.m.8:30 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Dumb and Drummer
Sep18
Music & Comedy, Theatre & Performing Arts

Dumb and Drummer

Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…

Thursday, September 18th
7:30 p.m.9:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
OhJay Lamont
Sep18
Music & Comedy

OhJay Lamont

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…

Thursday, September 18th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Teneisha Wilson at The Comedy Bar
Sep18
Music & Comedy

Teneisha Wilson at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Straight from your timeline to the…

Thursday, September 18th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Hot People Island
Sep18
Music & Comedy, Theatre & Performing Arts

Hot People Island

Hot People Island is a world premiere original comedy by Deana Velandra. In this play, a popular television network will take eight lucky certified Hot…

Thursday, September 18th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
Chicago Symphony Orchestra: Season Opening with Szeps-Znaider
Sep18
Music & Comedy, Theatre & Performing Arts

Chicago Symphony Orchestra: Season Opening with Szeps-Znaider

Overview One of the most heartfelt musical dialogues ever written, the Sinfonia concertante shows Mozart at the pinnacle of his craft. As violinist, Nikolaj Szeps-Znaider…

Thursday, September 18th
7:30 p.m.9:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
Improvsed DCOM
Sep18
Music & Comedy, Theatre & Performing Arts

Improvsed DCOM

Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…

Thursday, September 18th
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Lady Gaga – The Mayhem Ball Tour
Sep18
Music & Comedy

Lady Gaga – The Mayhem Ball Tour

After much anticipation, 14-time Grammy Award-winner Lady Gaga is heading out on ‘The MAYHEM Ball’ tour with stops at United Center on September 15, 17…

Thursday, September 18th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Sketch Playlist
Sep18
Music & Comedy, Theatre & Performing Arts

Sketch Playlist

Sketch Playlist is a weekly sketch show on Thursdays at 9:30pm at iO Theater (1501 N Kingsbury Street, Chicago 60642) that will feature brand-new material…

Thursday, September 18th
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
The 26th Anniversary Englewood Jazz Festival
Sep19
Festivals, Fairs & Special Events, Music & Comedy

The 26th Anniversary Englewood Jazz Festival

The 26th Annual Englewood Jazz Festival, presented by Live the Spirit Residency, returns to Chicago’s historic Hamilton Park on September 18–20, 2025, marking a powerful…

Friday, September 19th
Hamilton Park and Cultural Center
513 W 72nd St
Chicago Symphony Orchestra: Season Opening with Szeps-Znaider
Sep19
Music & Comedy, Theatre & Performing Arts

Chicago Symphony Orchestra: Season Opening with Szeps-Znaider

Overview One of the most heartfelt musical dialogues ever written, the Sinfonia concertante shows Mozart at the pinnacle of his craft. As violinist, Nikolaj Szeps-Znaider…

Friday, September 19th
1:30 p.m.3:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
The Infinite Wrench
Sep19
Music & 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…

Friday, September 19th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
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