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Upcoming Chicago Events

Check out what's happening all around Chicago.

Division Street Farmers Market
Oct1
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Wednesday, October 1st
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Lavelle Dontae at The Comedy Bar
Oct1
Music & Comedy

Lavelle Dontae at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Lavelle Dontae made his comedic debut…

Wednesday, October 1st
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Colter Wall and Friends
Oct1
Wednesday, October 1st
7:30 p.m.10:30 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Hooch & Holler Comedy Show
Oct1
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, October 1st
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Division Street Farmers Market
Oct2
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Thursday, October 2nd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
FashionBar The Shows: October 2025 – Trans Media Fashion
Oct2
Festivals, Fairs & Special Events, Theatre & Performing Arts

FashionBar The Shows: October 2025 – Trans Media Fashion

Trans Media Fashion celebrates diversity, inclusion, and self-expression, with collections created to amplify LGBTQ voices through fashion. This runway experience blends identity and artistry with…

Thursday, October 2nd
6:00 p.m.9:00 p.m.
Water Tower Place
835 N Michigan Ave
Clued In: Where There’s a Will, There’s a Way
Oct2
Music & Comedy, Theatre & Performing Arts

Clued In: Where There’s a Will, There’s a Way

YOU’RE INVITED…to bear witness to a fully improvised murder mystery. Six improvisers find themselves trapped on stage with a murderer, and nobody knows who the…

Thursday, October 2nd
7:00 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Teatro Zinzanni
Oct2
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, October 2nd
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The 4th Annual Latina Comedy Festival
Oct2
Music & Comedy

The 4th Annual Latina Comedy Festival

The Latina Comedy Festival is back! Join us October 2nd-4th in Chicago for a 3 day comedy extravanganza packed with shows, parties, and workshops celebrating…

Thursday, October 2nd
7:00 p.m.10:00 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
OhJay Lamont & Friends at The Comedy Bar
Oct2
Music & Comedy

OhJay Lamont & Friends at The Comedy Bar

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, October 2nd
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Improvsed DCOM
Oct2
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, October 2nd
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Wolfman of Wrigleyville – Horror Comedy Play
Oct2
Music & Comedy, Theatre & Performing Arts

The Wolfman of Wrigleyville – Horror Comedy Play

This 70-minute comedy set in 1927 follows an investigative journalist and her ex-girlfriend, a private eye, as they look into a series of murders that…

Thursday, October 2nd
8:00 p.m.9:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Chicago Comedy Hour
Oct2
Music & Comedy

Chicago Comedy Hour

The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…

Thursday, October 2nd
8:30 p.m.9:30 p.m.
Donny’s Skybox
230 W North Ave
Chicago Comedy Hour
Oct2
Music & Comedy, Theatre & Performing Arts

Chicago Comedy Hour

The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…

Thursday, October 2nd
8:30 p.m.9:30 p.m.
Donny’s Skybox
230 W North Ave
Sketch Playlist
Oct2
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, October 2nd
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Ear Taxi Festival
Oct3
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Friday, October 3rd
Division Street Farmers Market
Oct3
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Friday, October 3rd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Chicago Symphony Orchestra: Piccolo Play & Adagio for Strings
Oct3
Music & Comedy, Theatre & Performing Arts

Chicago Symphony Orchestra: Piccolo Play & Adagio for Strings

Overview Pergolesi’s sacred masterpiece, the Stabat Mater, is filled with gorgeous, spine-tingling music that explores the nature of grief, hope and healing. These emotions also course…

Friday, October 3rd
1:30 p.m.3:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
Ninth Annual Lincoln Park Wine Fest
Oct3
Festivals, Fairs & Special Events

Ninth Annual Lincoln Park Wine Fest

Wines from Around the World Featured at 9thAnnual Lincoln Park Wine Fest in Jonquil Park October 3-5 Wine tastings, a food and beverage market, sommeliers on hand…

Friday, October 3rd
5:00 p.m.10:00 p.m.
Jonquil Park
1001 W. Wrightwood Avenue
Wicker Park Bucktown’s “First Fridays” Art Walk
Oct3
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday, October 3rd
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
The Infinite Wrench
Oct3
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, October 3rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Oct3
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday, October 3rd
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Oct3
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday, October 3rd
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Ahamed Weinberg at The Comedy Bar
Oct3
Music & Comedy

Ahamed Weinberg at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Ahamed Weinberg is a Los Angeles-based…

Friday, October 3rd
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
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