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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, December 17th
7:00 p.m. – 9:00 p.m.The Comedy Bar
500 N. LaSalle St.Music & Comedy
Pink Martini All Stars
Thomas Lauderdale’s globe-trotting “little orchestra” Pink Martini is back with an all-new holiday show that brings triple the joy! Featuring three of the band’s favorite…
Wednesday, December 17th
7:00 p.m. – 10:00 p.m.Auditorium Theatre
50 East Ida B. Wells DriveMusic & Comedy
Chicago’s Best Stand Up
Welcome to Chicago’s Best Stand Up at The Laugh Factory – Chicago, featuring the hilarious talents of Chicago’s top comedians. Join us on December 26,…
Wednesday, December 17th
8:00 p.m. – 10:00 p.m.The Laugh Factory
175 N BroadwayMusic & 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, December 17th
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionMusic & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Thursday, December 18th
7:00 p.m. – 10:00 p.m.Teatro ZinZanni – Cambria Hotel
32 W Randolph StMusic & Comedy, Theatre & Performing Arts
Duluth: An Improvised Midwest Murder
Based on the hit FX show “Fargo”, Duluth takes audiences into the world of true crime in the Midwest. Each week, the cast of Duluth will improvise a…
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, December 18th
7:30 p.m. – 9:00 p.m.The Lincoln Lodge Theater
2040 N. Milwaukee Ave.Music & Comedy
Jason Ellis at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Born in Melbourne Australia, and now…
Thursday, December 18th
7:30 p.m. – 9:00 p.m.The Comedy Bar
500 N. LaSalle St.Music & Comedy
Happy Holly-Daze: A Holiday Drinking Game Performance
Year after year, Corn Productions brings the holiday magic in a tradition spanning over a decade. Happy Holly-Daze is a sketch comedy show about all…
Music & Comedy
Modi: Big Deal Comedy Fest
Don’t miss Modi, Elon Gold, and Michael Rapaport at the Big Deal Comedy Fest in Chicago on December 18th and Los Angeles on December 21st.
Thursday, December 18th
7:30 p.m. – 10:30 p.m.Auditorium Theatre
50 East Ida B. Wells DriveMusic & 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, December 18th
8:00 p.m. – 9:00 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy
Cafe Lounge Underwater Sketch Comedy Show
A night with Cafe Lounge Underwater is like the best house party you’ve ever been to. There’s dancing, music, drinks, and of course, meeting strangers…
Thursday, December 18th
8:00 p.m. – 9:00 p.m.Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.Music & Comedy, Theatre & Performing Arts
Class! with Sara Benincasa and Chad the Bird
No degree? No problem! Class is in session. Your nutty professors Sara Benincasa and Chad the Bird bring three geniuses to teach you stuff. Laugh…
Thursday, December 18th
8:00 p.m. – 10:00 p.m.The Lincoln Lodge
2040 N Milwaukee AveMusic & Comedy
CancerBlows Chicago
For the first time, CancerBlows comes to Chicago bringing its signature brand of music and hope through a special one-night concert event at Buddy Guy’s…
Thursday, December 18th
8:00 p.m. – 11:00 p.m.Buddy Guy’s Legends
700 S. WabashMusic & Comedy
Set In Chicago Holiday Style
Set In Chicago is back just in time for the holidays. This improvised movie sequel will now feature snow falling down and holiday cheer abound…
Thursday, December 18th
8:30 p.m. – 9:30 p.m.The Second City
1616 N. Wells St.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, December 18th
9:30 p.m. – 10:30 p.m.iO Theater
1501 N. Kingsbury St.Music & Comedy, Theatre & Performing Arts
Millennium Park Holiday Sing-Along
The Millennium Park Holiday Sing-Along invites Chicagoans and visitors to sing out and celebrate Chicago’s diverse holiday traditions at 6 p.m. on Fridays between December…
Friday, December 19th
6:00 p.m. – 7:00 p.m.Cloudgate Plaza in Millennium Park
201 E Randolph StMusic & 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, December 19th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.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, December 19th
7:00 p.m. – 8:30 p.m.Malarkey Comedy
1501 N. Kingsbury St.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, December 19th
7:00 p.m. – 8:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy
Jason Ellis at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Born in Melbourne Australia, and now…
Music & Comedy
Chicago’s Best Stand Up
Welcome to The Laugh Factory – Chicago, where laughter is guaranteed with Chicago’s Best Stand Up performing live on December 19, 2025, at 7:00 PM.…
Friday, December 19th
7:00 p.m. – 9:00 p.m.The Laugh Factory
175 N BroadwayMusic & Comedy
Crumb
Welcome to the Byline Bank Aragon Ballroom in Chicago, Illinois – where the magic of live music comes to life! Get ready for an unforgettable…
Friday, December 19th
7:00 p.m. – 9:00 p.m.Music & Comedy
The Black Angels
Welcome to the Byline Bank Aragon Ballroom in the vibrant city of Chicago, Illinois! On December 19, 2025, get ready to be mesmerized by the…
Friday, December 19th
7:00 p.m. – 9:00 p.m.

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