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Winter holiday events in Chicago, IL

Pawlidays Market
Sat, Dec 13, 11:00 AM
Chicago · Pup Social
Pawlidays Market
Sat, Dec 13, 11:00 AM
Chicago · Pup Social
Selling quickly
Burning Red’s 3rd Annual Christmas Birth-TAY Bash
Sat, Dec 13, 7:00 PM
Chicago · Theater on the Lake
Selling quickly
Burning Red’s 3rd Annual Christmas Birth-TAY Bash
Sat, Dec 13, 7:00 PM
Chicago · Theater on the Lake
Under the Misteltoe
Sat, Dec 20, 10:00 PM
Chicago · Hubbard Inn
Under the Misteltoe
Sat, Dec 20, 10:00 PM
Chicago · Hubbard Inn
Old Crow's Mimosas & Holiday Music Day Party - Includes 3 Hours of Mimosas!
Sat, Dec 6, 12:00 PM + 1 more
Chicago · Old Crow Smokehouse - Wrigleyville (AKA Santa's Workshop Pop-Up Bar)
Old Crow's Mimosas & Holiday Music Day Party - Includes 3 Hours of Mimosas!
Sat, Dec 6, 12:00 PM + 1 more
Chicago · Old Crow Smokehouse - Wrigleyville (AKA Santa's Workshop Pop-Up Bar)
✨ Jingle & Mingle: Chicago Holiday Hotel Lobby Tour ❄️
Today at 11:00 AM
Chicago · Millennium Hotel Knickerbocker Chicago
✨ Jingle & Mingle: Chicago Holiday Hotel Lobby Tour ❄️
Today at 11:00 AM
Chicago · Millennium Hotel Knickerbocker Chicago
2026 Chicago Winter Tequila Tasting Festival (February 14)
Sat, Feb 14, 2:30 PM
Chicago · King's
2026 Chicago Winter Tequila Tasting Festival (February 14)
Sat, Feb 14, 2:30 PM
Chicago · King's
Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier
Sun, Dec 21, 4:00 PM
Chicago · Old Crow Smokehouse - Wrigleyville
Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier
Sun, Dec 21, 4:00 PM
Chicago · Old Crow Smokehouse - Wrigleyville
CHRISTMAS MOVE + MERCADO
Sun, Dec 7, 9:30 AM
Forest Park · Casa Humilde Cerveceria & Cocina
CHRISTMAS MOVE + MERCADO
Sun, Dec 7, 9:30 AM
Forest Park · Casa Humilde Cerveceria & Cocina
Newport Theater Camp: Winter Act Development Courses
Chicago · The Newport Theater
Newport Theater Camp: Winter Act Development Courses
Chicago · The Newport Theater
The Official BAD SANTA Christmas Bar Crawl – Chicago
Sat, Dec 20, 3:00 PM
Chicago · West Hubbard Street
The Official BAD SANTA Christmas Bar Crawl – Chicago
Sat, Dec 20, 3:00 PM
Chicago · West Hubbard Street
Spice Up Your Winter Pepper Soup (Pepper Pot) :Water Side Market Place
Sun, Dec 7, 2:00 PM
Chicago · 2150 S Canalport Ave
Spice Up Your Winter Pepper Soup (Pepper Pot) :Water Side Market Place
Sun, Dec 7, 2:00 PM
Chicago · 2150 S Canalport Ave
Vox Venti With Guest Conductor Tim Lambert Presents "Guard My Tongue"
Sat, Dec 6, 7:30 PM
Chicago · Wicker Park Lutheran Church
Vox Venti With Guest Conductor Tim Lambert Presents "Guard My Tongue"
Sat, Dec 6, 7:30 PM
Chicago · Wicker Park Lutheran Church
Coochies For XXXMAS
Thu, Dec 18, 6:00 PM
Chicago · Dorothy
Coochies For XXXMAS
Thu, Dec 18, 6:00 PM
Chicago · Dorothy
New Year’s Eve: A Celebration at Terrace 16
Wed, Dec 31, 6:00 PM
Chicago · Terrace 16
New Year’s Eve: A Celebration at Terrace 16
Wed, Dec 31, 6:00 PM
Chicago · Terrace 16
Sleigh All Night
Fri, Dec 26, 10:00 PM
Chicago · Hubbard Inn
Sleigh All Night
Fri, Dec 26, 10:00 PM
Chicago · Hubbard Inn
Winter Wotaland
Today at 6:00 PM
Chicago · 4432 N Kedzie Ave #200
Winter Wotaland
Today at 6:00 PM
Chicago · 4432 N Kedzie Ave #200
Holiday Festa
Sat, Dec 13, 2:00 PM
Chicago · Eataly Chicago
Holiday Festa
Sat, Dec 13, 2:00 PM
Chicago · Eataly Chicago
SENSUAL N SEDUCTIVE: “THE SILENT NIGHT OF SEDUCTION” — CHRISTMAS EDITION
Sat, Dec 6, 8:00 PM
Chicago · 7458 S Langley Ave
SENSUAL N SEDUCTIVE: “THE SILENT NIGHT OF SEDUCTION” — CHRISTMAS EDITION
Sat, Dec 6, 8:00 PM
Chicago · 7458 S Langley Ave
Sales end soon
Wreath Making
Wednesday at 6:30 PM
Chicago · The CoCo Shop Chicago
Sales end soon
Wreath Making
Wednesday at 6:30 PM
Chicago · The CoCo Shop Chicago
Wreath Building Workshop with Vivant Gardening Services
Sun, Dec 14, 2:00 PM
Chicago · Dovetail Brewery
Wreath Building Workshop with Vivant Gardening Services
Sun, Dec 14, 2:00 PM
Chicago · Dovetail Brewery

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