Tue Dec 16, 2025
Carl Payne & Reginald Ballard
Venue: City Winery - Chicago
Time: 7:30 PM
Featuring: Carl Payne | Reginald Ballard!
Wed Dec 17, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Chicago's Best Stand Up
Thu Dec 18, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Funny Music Live - Stand Up Comics
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Funny Music Live - Stand Up Comics
Roast Battle Chicago
Venue: Zanies Comedy Club - Chicago
Time: 9:15 PM
Featuring: Roast Battle Chicago
Fri Dec 19, 2025
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Clued In - An Improvised Murder Mystery
Venue: Donny's Skybox Theatre at Second City - Chicago
Time: 7:00 PM
Featuring: Clued In - An Improvised Murder Mystery
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Chicago's Best Stand Up
Sat Dec 20, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Clued In - An Improvised Murder Mystery
Venue: Donny's Skybox Theatre at Second City - Chicago
Time: 7:00 PM
Featuring: Clued In - An Improvised Murder Mystery
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Chicago's Best Stand Up
The Nasty Show: Tiny Thickemz
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: The Nasty Show: Tiny Thickemz
Sun Dec 21, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
The Early Bird Special
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: The Early Bird Special
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Chicago's Best Stand Up
Angelo Colina - Spanish Performance
Venue: Zanies Comedy Club - Chicago
Time: 9:15 PM
Featuring: Angelo Colina
Mon Dec 22, 2025
Stand Ups Sit Down Comedy Showcase
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Stand Ups Sit Down Comedy Showcase
Tue Dec 23, 2025
Fresh Faces of Chicago
Venue: The Laugh Factory - Chicago
Time: 7:30 PM
Featuring: Fresh Faces of Chicago
Fri Dec 26, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 1:30 PM
Featuring: Second City Chicago: Rudolph Runs Wild
First Date Comedy Gameshow
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: First Date Comedy Gameshow
Clued In - An Improvised Murder Mystery
Venue: Donny's Skybox Theatre at Second City - Chicago
Time: 7:00 PM
Featuring: Clued In - An Improvised Murder Mystery
Something Unexpected
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Something Unexpected
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: Chicago's Best Stand Up
Sat Dec 27, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 1:30 PM
Featuring: Second City Chicago: Rudolph Runs Wild
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Clued In - An Improvised Murder Mystery
Venue: Donny's Skybox Theatre at Second City - Chicago
Time: 7:00 PM
Featuring: Clued In - An Improvised Murder Mystery
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:15 PM
Featuring: Chicago's Best Stand Up
The Nasty Show: Tiny Thickemz
Venue: The Laugh Factory - Chicago
Time: 11:30 PM
Featuring: The Nasty Show: Tiny Thickemz
Sun Dec 28, 2025
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 11:00 AM
Featuring: Second City Chicago: Rudolph Runs Wild
Second City Chicago: Rudolph Runs Wild
Venue: Mainstage at Second City - Chicago
Time: 1:30 PM
Featuring: Second City Chicago: Rudolph Runs Wild
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 7:00 PM
Featuring: Chicago's Best Stand Up
Chicago's Best Stand Up
Venue: The Laugh Factory - Chicago
Time: 9:00 PM
Featuring: Chicago's Best Stand Up
Mon Dec 29, 2025
Stand Ups Sit Down Comedy Showcase
Venue: The Laugh Factory - Chicago
Time: 8:00 PM
Featuring: Stand Ups Sit Down Comedy Showcase
Tue Dec 30, 2025
Fresh Faces of Chicago
Venue: The Laugh Factory - Chicago
Time: 7:30 PM
Featuring: Fresh Faces of Chicago
Wed Dec 31, 2025
Fri Jan 2, 2026
Sat Jan 3, 2026
Tue Jan 6, 2026
Thu Jan 8, 2026
Fri Jan 9, 2026
Sat Jan 10, 2026
Tue Jan 13, 2026
Thu Jan 15, 2026
Fri Jan 16, 2026
Sat Jan 17, 2026
Sun Jan 18, 2026
Wed Jan 21, 2026
Thu Jan 22, 2026
Fri Jan 23, 2026
Sat Jan 24, 2026
Sun Jan 25, 2026
Wed Jan 28, 2026
Tori Piskin - Comedian
Venue: Zanies Comedy Club - Chicago
Time: 7:00 PM
Featuring: Tori Piskin - Comedian
Thu Jan 29, 2026
Alex English - Comedian
Venue: Zanies Comedy Club - Chicago
Time: 7:00 PM
Featuring: Alex English - Comedian
Fri Jan 30, 2026
Alex English - Comedian
Venue: Zanies Comedy Club - Chicago
Time: 7:00 PM
Featuring: Alex English - Comedian
Alex English - Comedian
Venue: Zanies Comedy Club - Chicago
Time: 9:15 PM
Featuring: Alex English - Comedian
Sat Jan 31, 2026
Alex English - Comedian
Venue: Zanies Comedy Club - Chicago
Time: 7:00 PM
Featuring: Alex English - Comedian
Alex English - Comedian
Venue: Zanies Comedy Club - Chicago
Time: 9:15 PM
Featuring: Alex English - Comedian
Thu Feb 5, 2026
Fri Feb 6, 2026
Sat Feb 7, 2026
Chicago Comedy Show Information
- Schedule for the Comedy shows in Chicago is revised up to the minute.
- House Of Blues - Chicago and The Comedysportz Theatre both have lots of Comedy show activity coming up.
- Chicago remains one of the top locations for Comedy show tours in the US.
- Comedy Show Schedule will be some of the most anticipated Chicago Comedy shows by far.
- Tickets for all Chicago Comedy shows are protected with a 100% moneyback guarantee.
Chicago so far has a massive list of Comedy show tours visiting Chicago in the coming weeks. A selection of Comedy music's top tours are about to have shows in Chicago. Make sure to catch some of the Comedy show excitement that Chicago has to offer at some of the best venues around. Just check out the list here for all the best Chicago Comedy shows. Our Chicago show schedule is updated on a regular basis in case their are any adjustments.
