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Chicago Winter Activities
By popularity
By popularity
By date
Type
Type
Music
Performing Arts
Sports & Outdoors
Comedy
Meetup
Sponsored
360 Chicago Observation Deck With Tilt
Sponsored
360chicago.com
.
from
$45
4.6/5
(9861)
Curbside Sedan Transfer From O`Hare/Midway To Downtown Chicago
Sponsored
viator.com
.
from
$195
DEC
1
MON
Destroy Lonely
MUSIC
Aragon Ballroom
7:00 PM ·
$442
DEC
2
TUE
Dave Herrero
MUSIC
Rosa's Lounge
9:00 PM
DEC
3
WED
Kyle Swan Trio
MUSIC
The Jazz Showcase
8:00 PM ·
$52
DEC
4
THU
TBA/TBA
BLUES MUSIC
Kingston Mines
6:00 PM
DEC
5
FRI
the hoyle brothers @ Empty Bottle
COUNTRY MUSIC
The Empty Bottle
5:30 PM
DEC
5
FRI
Dave Herrero
MUSIC
Sheraton Grand Chicago Riverwalk
4:00 PM
DEC
4
THU
Wait Wait... Don't Tell Me Podcast - Chi…
PLAY
Studebaker Theater
7:30 PM
DEC
10
WED
Folk You! December 2025
MUSIC
Montrose Saloon
7:00 PM
DEC
9
TUE
Northwestern Medicine Brain Aneurysm Support Group
OTHERS
Northwestern Medicine
8:00 AM
DEC
11
THU
Liquid Mike
MUSIC
Concord Music Hall
7:00 PM
DEC
12
FRI
Acid Bath with High On Fire
ROCK MUSIC
The Salt Shed - Indoors
8:00 PM
DEC
13
SAT
Origami Open House
OTHERS
Garfield Park
12:00 PM
DEC
14
SUN
SF Duo
MUSIC
Vincent
7:00 PM
DEC
20
SAT
Chicago Philharmonic: The Holiday in …
MUSIC
Auditorium Theatre
7:30 PM ·
$73
DEC
20
SAT
Bryan Eng @ Winter's Jazz Club
MUSIC
Winter's Jazz Club
7:00 PM
DEC
20
SAT
Bryan Eng Trio
MUSIC
Winter's Jazz Club
9:00 PM
DEC
20
SAT
Zeds Dead
MUSIC
Concord Music Hall
11:00 PM
