Things to do in Chicago in December 2026 – page 4

House Calls 'In the Round' with Enzo Siragusa

Sat, Dec 5 · 9:00 PM

Thalia Hall

From $20.03

Kelsey Cook

Sat, Dec 5 · 9:15 PM

The Den Theatre

Leslie Liao

Sat, Dec 5 · 9:15 PM

Zanies Comedy Club

Ginger Road

Sat, Dec 5 · 9:30 PM

Carol's Pub

From $12.08

Eric Prydz - Ages 18+

Sat, Dec 5 · 10:00 PM

Radius

Bears vs Jaguars At The Bottle

Sun, Dec 6 · 12:00 PM

The Empty Bottle

Chicago Bears vs. Jacksonville Jaguars

Sun, Dec 6 · 12:00 PM

Soldier Field

UIC Flames Men's Basketball v Calumet College of St. Joseph

Sun, Dec 6 · 2:00 PM

Credit Union 1 Arena at UIC

A Christmas Carol - Open Captioned

Sun, Dec 6 · 2:00 PM

Goodman Theatre - Albert

Lukas Sternath

Sun, Dec 6 · 3:00 PM

Symphony Center

Michael Blaustein

Sun, Dec 6 · 5:00 PM

Vic Theatre

Mike Wheeler Blues Band/Rico McFarland Blues Band

Dec 6–7, 2026

Kingston Mines - Chicago Blues Center

From $18

Chicago Blackhawks vs. Edmonton Oilers

Dec 6, 2026 and Mar 1, 2027

United Center

Parvati and Cirie (18 and Over)

Sun, Dec 6 · 6:00 PM

Vic Theatre

Smith & Myers

Sun, Dec 6 · 6:30 PM

House of Blues Chicago

The Jinkx & DeLa Holiday Show

Sun, Dec 6 · 7:00 PM

The Auditorium

A Christmas Carol - In Spanish

Sun, Dec 6 · 7:00 PM

Goodman Theatre - Albert

Leslie Liao

Sun, Dec 6 · 7:00 PM

Zanies Comedy Club

Jamila Woods: 10 Years of HEAVN featuring support from Ayanna Woods and a Sound Bath led by Shawnee Dez hosted by Raych Jackson

Sun, Dec 6 · 8:00 PM

Thalia Hall

From $51.08

Xlov

Sun, Dec 6 · 8:00 PM

Copernicus Center

Whitmer Thomas with comedy from Clay Tatum

Sun, Dec 6 · 9:00 PM

The Empty Bottle

Wilco

Dec 7 and 8, 2026

Thalia Hall

FREE MONDAY w/ Answering Machines / Oildrum / Pebbles Inc

Mon, Dec 7 · 9:00 PM

The Empty Bottle

The Unauthorized Hallmark(ish) Parody Musical

Dec 7–12, 2026

Broadway Playhouse at Water Tower Place