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Music & 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 16th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveMusic & Comedy
Tomato Throw Show
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…
Festivals, Fairs & Special Events, Tours & Attractions
Krampus: The Fright Before Christmas
We have transformed our haunted house into a Christmas wonderland, although it won’t be all glitter and snowflakes. You better watch out. You better not…
Music & Comedy
Fresh Faces of Chicago
Welcome to The Laugh Factory – Chicago, where the vibrant city of Chicago comes alive with the Fresh Faces of Chicago on December 16, 2025,…
Tuesday, December 16th
7:30 p.m. – 9:30 p.m.The Laugh Factory
175 N BroadwayFestivals, Fairs & Special Events, Tours & Attractions
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Join American Ghost Walks on a spine-chilling Chicago Ghost Tour & Ghost Hunt in Lincoln Park, known for its eerie hauntings and chilling history. Dive…
Tuesday, December 16th
8:00 p.m. – 10:00 p.m.Meeting Point: In front of the Chicago History Museum
1601 N Clark St.Music & Comedy
Rod Wave – The Redemption Experience 2025-26 Tour
Rod Wave is scheduled to perform two shows in Chicago at the United Center as part of his Redemption Experience Tour in December 2025.
Festivals, Fairs & Special Events
Letter to Santa
Little ones are invited to share their holiday wishes in our beautifully decorated lobby. Children can pen letters to Santa and place them in our…
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions
Evanston Art Center’s 23nd Annual Winter Arts & Crafts Expo
The Evanston Art Center is proud to present the 23rd annual Winter Arts & Crafts Expo, featuring one-of-a-kind pieces of work by over 160 selected…
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions
Paris in Black Exhibition Opening at the DuSable Museum
Join us at the DuSable Black History Museum and Education Center for the opening of Paris in Black: Internationalism and the Black Renaissance. Discover the…
Wednesday, December 17thDuSable Museum of African American History
740 East 56th PlaceFestivals, Fairs & Special Events
Holidays at Skydeck!
HOLIDAYS @ SKYDECK CHICAGO! Celebrate the season from 103 stories above the city at Holidays @ Skydeck! Skydeck’s lower-level Chicago museum and observation deck will…
Festivals, Fairs & Special Events
Christkindlmarket
What can you expect at the market? The German-style Christmas Market provides a safe outdoor experience for the whole family. All Christkindlmarkets are always free admission. The smell of roasted nuts,…
Wednesday, December 17th
11:00 a.m. – 9:00 p.m.Daley Civic Center
50 W. Washington St.Festivals, Fairs & Special Events
Holiday Magic
We’re lighting up the night this holiday season! Returning with a brand new light display, celebrate more than 40 years of Holiday Magic. Now with…
Wednesday, December 17th
3:00 p.m. – 9:00 p.m.Brookfield Zoo Chicago
3300 Golf RdFestivals, Fairs & Special Events
Sheraton Sleigh Bar, Presented by Shula’s Steak House
Celebrate the holidays in Chicago at the Sheraton Sleigh Bar, presented by Shula’s Steak House—a limited-time holiday pop-up bar located inside the Sheraton Grand Chicago Riverwalk. This festive…
Wednesday, December 17th
5:30 p.m. – 9:00 p.m.Sheraton Grand Chicago Riverwalk
301 E. North Water StreetMusic & 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 DriveFestivals, Fairs & Special Events, Tours & Attractions
Krampus: The Fright Before Christmas
We have transformed our haunted house into a Christmas wonderland, although it won’t be all glitter and snowflakes. You better watch out. You better not…
Wednesday, December 17th
7:00 p.m. – 10:00 p.m.13th Floor Chicago
5050 River RdMusic & Comedy
Chicago’s Late Night Talk Show: Christmas Special
The Not That Late Show is a POC- and queer-led late-night talk show hosted by Justin Swinson, featuring an ensemble of Chicago comedians debuting brand-new…
Wednesday, December 17th
7:30 p.m. – 9:00 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueFestivals, Fairs & Special Events, Tours & Attractions
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Join American Ghost Walks on a spine-chilling Chicago Ghost Tour & Ghost Hunt in Lincoln Park, known for its eerie hauntings and chilling history. Dive…
Wednesday, December 17th
8:00 p.m. – 10:00 p.m.Meeting Point: In front of the Chicago History Museum
1601 N Clark St.Music & 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 DivisionFestivals, Fairs & Special Events
Letter to Santa
Little ones are invited to share their holiday wishes in our beautifully decorated lobby. Children can pen letters to Santa and place them in our…
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions
Evanston Art Center’s 23nd Annual Winter Arts & Crafts Expo
The Evanston Art Center is proud to present the 23rd annual Winter Arts & Crafts Expo, featuring one-of-a-kind pieces of work by over 160 selected…
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions
Paris in Black Exhibition Opening at the DuSable Museum
Join us at the DuSable Black History Museum and Education Center for the opening of Paris in Black: Internationalism and the Black Renaissance. Discover the…
Thursday, December 18thDuSable Museum of African American History
740 East 56th PlaceFestivals, Fairs & Special Events
Holidays at Skydeck!
HOLIDAYS @ SKYDECK CHICAGO! Celebrate the season from 103 stories above the city at Holidays @ Skydeck! Skydeck’s lower-level Chicago museum and observation deck will…

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