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Music & Comedy
Chicago’s Best Stand Up
Welcome to Chicago’s Best Stand Up at The Laugh Factory – Chicago, featuring some of the city’s finest comedians. Get ready for a night of…
Sunday, December 28th
9:00 p.m. – 11:00 p.m.The Laugh Factory
175 N BroadwayMusic & Comedy
Chicago’s Best Stand Up
Welcome to Chicago’s Best Stand Up at The Laugh Factory – Chicago! Join us on December 28, 2025, at 9:00 PM for a night of…
Sunday, December 28th
9:00 p.m. – 11:00 p.m.The Laugh Factory
175 N BroadwayTheatre & Performing Arts
The Phantom of the Opera
THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…
Monday, December 29thCadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601Theatre & Performing Arts
A Christmas Carol
“I will honor Christmas in my heart, and try to keep it all the year.” Rediscover a Dickens’ classic with an adaptation that “makes you…
Monday, December 29th
2:00 p.m.Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601Music & Comedy
Raheem DeVaughn – 20 Lessons of Love Tour
Get ready for a night of soulful vibrancy as multi‑platinum R&B artist Raheem DeVaughn heads to Chicago. Known for his silky vocals and heartfelt lyrics,…
Monday, December 29th
6:00 p.m. – 11:30 p.m.City Winery
1200 West Randolph StreetMusic & Comedy, Theatre & Performing Arts
Clayton Horwitz at Zanies Chicago – Live Comedy Taping!
CLAY HORWITZ is an NYC comedian originally from Chicago. He is the star and writer of the show Clay’s Feast on Amazon Prime Video, and…
Monday, December 29th
7:00 p.m. – 8:30 p.m.Zanies Comedy Night Club
1548 North Wells StreetMusic & 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…
Monday, December 29th
7:00 p.m. – 10:00 p.m.Teatro ZinZanni – Cambria Hotel
32 W Randolph StTheatre & Performing Arts
Amadeus
Vienna: a cacophony of music and intrigue. The emperor’s composer, Antonio Salieri, holds court until the flamboyant entrance of Wolfgang Amadeus Mozart: prodigy and wild…
Monday, December 29th
7:30 p.m.Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614Music & Comedy
Stand Ups Sit Down Comedy Showcase
Welcome to The Laugh Factory in Chicago, Illinois – the ultimate hotspot for comedy lovers! Join us on December 29, 2025, at 8:00 PM for…
Monday, December 29th
8:00 p.m. – 10:00 p.m.The Laugh Factory
175 N BroadwayTheatre & Performing Arts
The Phantom of the Opera
THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…
Tuesday, December 30thCadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601Theatre & Performing Arts
A Christmas Carol
“I will honor Christmas in my heart, and try to keep it all the year.” Rediscover a Dickens’ classic with an adaptation that “makes you…
Tuesday, December 30th
2:00 p.m.Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601Music & Comedy, Theatre & Performing Arts
Improvised Christmas Carol
In a cuckoo-bananas world, sometimes we all just need a good ‘ol fashion morality check. It’s time for Ebenezer Scrooge to get another supernatural wake-up…
Tuesday, December 30th
7:00 p.m. – 8:00 p.m.The Second City
230 W North Ave., 2nd FloorMusic & 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, December 30th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveTheatre & Performing Arts
Amadeus
Vienna: a cacophony of music and intrigue. The emperor’s composer, Antonio Salieri, holds court until the flamboyant entrance of Wolfgang Amadeus Mozart: prodigy and wild…
Tuesday, December 30th
7:30 p.m.Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614Music & Comedy
Fresh Faces of Chicago
Welcome to The Ground Name, your go-to destination for live events in Chicago, Illinois! Join us on December 30, 2025, at 7:30 PM for an…
Tuesday, December 30th
7:30 p.m. – 9:30 p.m.The Laugh Factory
175 N BroadwayTheatre & Performing Arts
The Phantom of the Opera
THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…
Wednesday, December 31stCadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601Theatre & Performing Arts
A Christmas Carol
“I will honor Christmas in my heart, and try to keep it all the year.” Rediscover a Dickens’ classic with an adaptation that “makes you…
Wednesday, December 31st
2:00 p.m.Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601Music & Comedy
Jeff Dunham: Artificial Intelligence Tour
Comedian and ventriloquist Jeff Dunham lights up the stage at Allstate Arena in Rosemont, IL, on December 31, 2025, as part of his Artificial Intelligence Tour. His infamous characters…
Wednesday, December 31st
3:00 p.m. – 5:00 p.m.Allstate Arena
6920 Mannheim RoadMusic & 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…
Wednesday, December 31st
7:00 p.m. – 10:00 p.m.Teatro ZinZanni – Cambria Hotel
32 W Randolph StMusic & Comedy
Dru Hill: Tell Me it’s New Years Eve!
Get ready, Chicago — the smooth‑and‑soulful harmony of Dru Hill is hitting the Windy City! Known for their R&B anthems like In My Bed and How Deep Is Your Love, Dru Hill…
Wednesday, December 31st
7:00 p.m. – 11:30 p.m.City Winery
1200 West Randolph StreetFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Music & Comedy, Tours & Attractions
NYAvlí at Avlí On The Park
NYAvlí isn’t just a reservation; it’s the annual tradition you didn’t know you were missing! Revel in Lakeshore East’s most beautiful dining room + event…
Wednesday December 31, 2025
7:00 p.m. – Thursday January 1, 2026
1:30 a.m.Avli On The Park
180 N Field BlvdTheatre & Performing Arts
Amadeus
Vienna: a cacophony of music and intrigue. The emperor’s composer, Antonio Salieri, holds court until the flamboyant entrance of Wolfgang Amadeus Mozart: prodigy and wild…
Wednesday, December 31st
7:30 p.m.Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614Music & Comedy
New Years Eve Comedy Show
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Looking for things to do on…
Wednesday, December 31st
8:00 p.m. – 9:30 p.m.The Comedy Bar
500 N. LaSalle St.Music & Comedy
DeRay Davis Annual Funny & Famous Chi Town Comedy Count Down
End 2025 on a high note with this not-to-be-missed event – the return of DeRay Davis’ Funny and Famous Chi Town Comedy Countdown! Featuring DeRay Davis with…
Wednesday, December 31st
8:00 p.m. – 11:00 p.m.Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore Dr

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