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Published on OCT 23, 2026
Chicago's Ultimate 2026 Holiday Bucket List
The temperatures may be dropping, but the winter activities in Chicago are just starting to heat up! Check out this year's ultimate winter bucket list. ☃️ ❄️
By Chicago Bucket List
Recommended Experiences
BYOB Wine Glass Painting + Charm Making Night
NOV 4 - FEB 26
From
Dazed & Infused Comedy Brunch
SATURDAY
From
EXCLUSIVE
Holly Jolly Christmas Bar at Everything Bar - Chicago
NOV 12 - DEC 27
From
PRESENTS
Mariah Carey's Holiday Bar at Experience 868 - Chicago
NOV 19 - DEC 27
From
PRESENTS
Santa Baby Bar
NOV 20 - JAN 3
From
EXCLUSIVE
Rug Tufting Workshop - Chicago (Up to 10% off!)
NOV 3 - DEC 31
From
$96
4% OFF
BEST PRICE
Your Private Chef Awaits: 15-Course Omakase in a Hotel Suite
NOV 3 - 30
From
EXCLUSIVE
Make Scents on Mag Mile - Candle and Perfume Making Classes
NOV 3 - DEC 31
From
DIY Pizza & SIP
NOV 3 - DEC 30
From
Pumpkin Candle Making & Intentional Perfume Workshops (up to 18% off)
NOV 3 - DEC 31
From
$61
19% OFF
BEST PRICE
BYOB Wine Glass Painting + Charm Making Night
NOV 4 - FEB 26
From
Dazed & Infused Comedy Brunch
SATURDAY
From
EXCLUSIVE
Holly Jolly Christmas Bar at Everything Bar - Chicago
NOV 12 - DEC 27
From
PRESENTS
Mariah Carey's Holiday Bar at Experience 868 - Chicago
NOV 19 - DEC 27
From
PRESENTS
Santa Baby Bar
NOV 20 - JAN 3
From
EXCLUSIVE
Rug Tufting Workshop - Chicago (Up to 10% off!)
NOV 3 - DEC 31
From
$96
4% OFF
BEST PRICE
Your Private Chef Awaits: 15-Course Omakase in a Hotel Suite
NOV 3 - 30
From
EXCLUSIVE
Make Scents on Mag Mile - Candle and Perfume Making Classes
NOV 3 - DEC 31
From
DIY Pizza & SIP
NOV 3 - DEC 30
From
Pumpkin Candle Making & Intentional Perfume Workshops (up to 18% off)
NOV 3 - DEC 31
From
$61
19% OFF
BEST PRICE
BYOB Wine Glass Painting + Charm Making Night
NOV 4 - FEB 26
From
Dazed & Infused Comedy Brunch
SATURDAY
From
EXCLUSIVE
Holly Jolly Christmas Bar at Everything Bar - Chicago
NOV 12 - DEC 27
From
PRESENTS
Mariah Carey's Holiday Bar at Experience 868 - Chicago
NOV 19 - DEC 27
From
PRESENTS
Santa Baby Bar
NOV 20 - JAN 3
From
EXCLUSIVE
Rug Tufting Workshop - Chicago (Up to 10% off!)
NOV 3 - DEC 31
From
$96
4% OFF
BEST PRICE
Your Private Chef Awaits: 15-Course Omakase in a Hotel Suite
NOV 3 - 30
From
EXCLUSIVE
Make Scents on Mag Mile - Candle and Perfume Making Classes
NOV 3 - DEC 31
From
DIY Pizza & SIP
NOV 3 - DEC 30
From
Pumpkin Candle Making & Intentional Perfume Workshops (up to 18% off)
NOV 3 - DEC 31
From
$61
19% OFF
BEST PRICE
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