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Winter holiday events in Chesterton, IN

Pop & Shop Holiday Champagne Tasting
Fri, Dec 12, 6:00 PM
Westville · Blue Moon Barn & Vintage Market
Pop & Shop Holiday Champagne Tasting
Fri, Dec 12, 6:00 PM
Westville · Blue Moon Barn & Vintage Market
Sales end soon
HOLIDAY HOOPLA at 4 CORNERS WINERY
Saturday at 11:30 AM
Valparaiso · Four Corners Winery
Sales end soon
HOLIDAY HOOPLA at 4 CORNERS WINERY
Saturday at 11:30 AM
Valparaiso · Four Corners Winery
From The Page : A New Story Series
Sun, Dec 7, 7:00 PM
Chicago · 3658 N Pulaski Rd
From The Page : A New Story Series
Sun, Dec 7, 7:00 PM
Chicago · 3658 N Pulaski Rd
Sales end soon
Holiday Cheer Christmas Cookie Decorating Class!
Friday at 3:30 PM
Valparaiso · Parlor Doughnuts
Sales end soon
Holiday Cheer Christmas Cookie Decorating Class!
Friday at 3:30 PM
Valparaiso · Parlor Doughnuts
Winter Breads Baking Class
Sun, Dec 7, 10:30 AM
Chicago · Bettie's Chicago
Winter Breads Baking Class
Sun, Dec 7, 10:30 AM
Chicago · Bettie's Chicago
Xmas vibe
Sat, Dec 6, 8:00 PM
Dolton · Dolton Bowl
Xmas vibe
Sat, Dec 6, 8:00 PM
Dolton · Dolton Bowl
Chicago Santa Bar Crawl
Sat, Dec 20, 1:00 PM
Chicago · Kaiser Tiger
Chicago Santa Bar Crawl
Sat, Dec 20, 1:00 PM
Chicago · Kaiser Tiger
Winter Solstice Immersive Sound Healing Ceremony with Davin Youngs
Sun, Dec 21, 7:00 PM
Chicago · The Joinery
Winter Solstice Immersive Sound Healing Ceremony with Davin Youngs
Sun, Dec 21, 7:00 PM
Chicago · The Joinery
Nearly full
Breakfast with Santa at Aster Hall | 900 N. Michigan Shops
Sat, Dec 13, 9:00 AM
Chicago · 900 North Michigan Shops
Nearly full
Breakfast with Santa at Aster Hall | 900 N. Michigan Shops
Sat, Dec 13, 9:00 AM
Chicago · 900 North Michigan Shops
Just added!
SENSUAL N SEDUCTIVE: “THE SILENT NIGHT OF SEDUCTION” — CHRISTMAS EDITION
Sat, Dec 6, 8:00 PM
Chicago · 7458 S Langley Ave
Just added!
SENSUAL N SEDUCTIVE: “THE SILENT NIGHT OF SEDUCTION” — CHRISTMAS EDITION
Sat, Dec 6, 8:00 PM
Chicago · 7458 S Langley Ave
Just added!
Little Chef's Holiday Donut Decorating
Sat, Dec 13, 12:00 PM
Chicago · Time Out Market Chicago
Just added!
Little Chef's Holiday Donut Decorating
Sat, Dec 13, 12:00 PM
Chicago · Time Out Market Chicago
Below The Waist Presents: A Holiday Bouquet Making Class
Sun, Dec 14, 1:00 PM
Highland · Willow Blooms
Below The Waist Presents: A Holiday Bouquet Making Class
Sun, Dec 14, 1:00 PM
Highland · Willow Blooms
Friendsmas Holiday Pajama Party
Sat, Dec 13, 5:00 PM
Chicago · IN SESSION Sound.bite Lounge
Friendsmas Holiday Pajama Party
Sat, Dec 13, 5:00 PM
Chicago · IN SESSION Sound.bite Lounge
AirOtic presents Naughty Noël
Thu, Dec 4, 7:00 PM + 13 more
Chicago · Experience 868 Events
AirOtic presents Naughty Noël
Thu, Dec 4, 7:00 PM + 13 more
Chicago · Experience 868 Events
Sales end soon
Holiday Pop Up Picture Day November 28-30, 2025
Friday at 8:00 AM + 101 more
Chesterton · Spare Room Studios
Sales end soon
Holiday Pop Up Picture Day November 28-30, 2025
Friday at 8:00 AM + 101 more
Chesterton · Spare Room Studios
Holiday Jazz Concert
Thu, Dec 4, 6:30 PM
Burr Ridge · Burr Ridge Community Church
Holiday Jazz Concert
Thu, Dec 4, 6:30 PM
Burr Ridge · Burr Ridge Community Church
Cocktails x Crafts: Winter Wreath Workshop
Thu, Dec 4, 6:00 PM
Chicago · Fora
Cocktails x Crafts: Winter Wreath Workshop
Thu, Dec 4, 6:00 PM
Chicago · Fora
Sales end soon
Crawl To Christkindlmarket Wrigleyvile: A Holiday Pop-Up Bar Crawl
Friday at 5:00 PM + 14 more
Chicago · Wrigleyville Wonderland
Sales end soon
Crawl To Christkindlmarket Wrigleyvile: A Holiday Pop-Up Bar Crawl
Friday at 5:00 PM + 14 more
Chicago · Wrigleyville Wonderland
A Spirited Affair: Winter Floral Workshop & Wine Pairing with Prisoner Wine
Wed, Dec 10, 6:00 PM
Chicago · The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
A Spirited Affair: Winter Floral Workshop & Wine Pairing with Prisoner Wine
Wed, Dec 10, 6:00 PM
Chicago · The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Chicago Official Ugly Sweater Bar Crawl
Sat, Dec 20, 1:00 PM
Chicago · Kaiser Tiger
Chicago Official Ugly Sweater Bar Crawl
Sat, Dec 20, 1:00 PM
Chicago · Kaiser Tiger

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