Things to do in Chicago on Sunday, December 20, 2026

28 events listed in and around Chicago, each with its time and venue.

Morning

December Free Day at the American Writers Museum
Museum & Gallery · 10 AM – 5 PM · The Loop
Balloon Museum | EmotionAir - Art You Can Feel - Chicago
Museum & Gallery · 10:15 AM · Belmont Gardens
A Charlie Brown Christmas Brunch LIVE w/ CHRIS WHITE TRIO! **Tickets on sale Friday, 10/2 at 10am**
Live Music · Jazz · 11 AM · FITZGERALDS NIGHTCLUB
FITZKINDLE MARKET: A Christmas Tree Lot & Holiiday Extravaganza!
Market · Christmas Tree · 11 AM · FITZGERALDS NIGHTCLUB
Bluey's Big Play (Chicago)
Family Show · 11 AM · The Loop

Afternoon

Weed Passport Tours: North Michigan Ave Experience
Tour · 12 PM · Fulton River District
Potted Potter (Chicago)
Comedy · 1 PM · Magnificent Mile
A Brunch of Drag
Drag & Burlesque · 1 PM – 4 PM · Pilsen
Dr. Seuss' How the Grinch Stole Christmas the Musical (Chicago)
Musical · 1 PM · The Loop
A Charlie Brown Christmas Brunch LIVE w/ CHRIS WHITE TRIO! **Tickets on sale Friday, 10/2**
Live Music · 1 PM · FITZGERALDS NIGHTCLUB
PBR: Unleash the Beast
Sports · 1:45 PM · United Center
UIC Flames Women's Basketball v Indiana State
Game · Basketball · 2 PM · Credit Union 1 Arena at UIC
Vape! The Grease Parody
Musical · 2:30 PM · Wrightwood Neighbors
SUNDAY DAYDREAM: Celebrating the Grateful Dead
Cover Band · 3:30 PM · FITZGERALDS NIGHTCLUB
Dance To Heal
Dance Fitness · 3:30 PM · Drucker Center

Evening

Baby Smoove Live!
Live Music · 5 PM · The Loop
December Book Club w/ Three Avenues: Back Where We Started
Book Club · 5 PM · Lincoln Park
Harvest Diner
Food & Drink · 5 PM – 9 PM · South Loop
Mike Wheeler Blues Band/Rico McFarland Blues Band
Concert · Blues · 5:30 PM – 1 AM · Kingston Mines - Chicago Blues Center
Relix Presents: An Intimate Evening with Moe.
Live Music · 7 PM · Near West Side
BIG BAND & BBQ: Chicago Skyliner's w/ Bill O'Connell
Live Music · Jazz · 7 PM · FITZGERALDS NIGHTCLUB
Mariachi Herencia De México - A Mariachi Christmas
Live Music · Latin · 7 PM · Pilsen
SOLSTICE: An Immersive Sound Healing Experience with Davin Youngs
Meditation · 7 PM · Logan Square
2026 ONEUS World Tour: Full Moon
Live Music · 7:30 PM · Copernicus Center
Myq Kaplan Does the Best Stand-Up Comedy You've Never Seen!
Stand-up · 8 PM · Logan Square
JUKE PARTY CHICAGO: THE ENCORE — BACK BY POPULAR DEMAND
Dance Party · Electronic · 8 PM – 1 AM · Little Village
Marti & Mimi's "Back to School" Charity Ball
Variety Show · 8:30 PM · Lakeview
Oscarbate Film Collective Presents: The All-Chicago Tenants Alliance Fundraiser
Volunteering · 9 PM · Ukrainian Village
All things to do in Chicago