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Winter holiday Events and Things to do in Chicago, IL

FashionCamp: WINTER HOLIDAY EDITION 2026
Sat, Dec 12, 10:00 AM
Chicago · FashionBar (Level 3)
FashionCamp: WINTER HOLIDAY EDITION 2026
Sat, Dec 12, 10:00 AM
Chicago · FashionBar (Level 3)
Going fast
End of Winter Kickball!
Saturday at 12:00 PM
Chicago · Chase Park
Going fast
End of Winter Kickball!
Saturday at 12:00 PM
Chicago · Chase Park
Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series
Sun, Dec 6, 12:00 PM
Chicago · Goose Island Taproom
Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series
Sun, Dec 6, 12:00 PM
Chicago · Goose Island Taproom
Powder: A Winter Après-Ski Party
Sat, Mar 28, 1:00 PM
Chicago · Recess
Powder: A Winter Après-Ski Party
Sat, Mar 28, 1:00 PM
Chicago · Recess
Sales end soon
Late Winter Dinner Party Series: A Local, Seasonal, Communal Meal
Saturday at 7:00 PM
Chicago · Trogo Kitchen and Market
Sales end soon
Late Winter Dinner Party Series: A Local, Seasonal, Communal Meal
Saturday at 7:00 PM
Chicago · Trogo Kitchen and Market
Daily Stoic Live | Onstage with Ryan Holiday
Wed, Aug 19, 7:00 PM
Chicago · Gateway Theater at Copernicus Center
Daily Stoic Live | Onstage with Ryan Holiday
Wed, Aug 19, 7:00 PM
Chicago · Gateway Theater at Copernicus Center
Limited Tickets - 2027 Chicago Winter Tequila Tasting Festival (February 20)
Sat, Feb 20, 2:30 PM
Chicago · King's
Limited Tickets - 2027 Chicago Winter Tequila Tasting Festival (February 20)
Sat, Feb 20, 2:30 PM
Chicago · King's
Almost full
Irene Phillips and Gabi Winter
Thu, Apr 16, 7:00 PM
Chicago · UncommonGround - Lakeview
Almost full
Irene Phillips and Gabi Winter
Thu, Apr 16, 7:00 PM
Chicago · UncommonGround - Lakeview
Late Winter Dinner Party Series: Paella
Thu, Apr 9, 6:30 PM
Chicago · Trogo Kitchen and Market
Late Winter Dinner Party Series: Paella
Thu, Apr 9, 6:30 PM
Chicago · Trogo Kitchen and Market
✨Candlelight Pink Full Moon Sound Bath✨
Thu, Apr 2, 7:00 PM
Chicago · 1229 N North Branch St
✨Candlelight Pink Full Moon Sound Bath✨
Thu, Apr 2, 7:00 PM
Chicago · 1229 N North Branch St
Easter Brunch at The Holiday Inn Skokie
Sun, Apr 5, 10:00 AM
Skokie · Holiday Inn Chicago North Shore (Skokie)
Easter Brunch at The Holiday Inn Skokie
Sun, Apr 5, 10:00 AM
Skokie · Holiday Inn Chicago North Shore (Skokie)
Sales end soon
Soul Glow — Spring Reset: Workshops & Night Market
Sunday at 10:00 AM
Chicago · Sanctuary Health
Sales end soon
Soul Glow — Spring Reset: Workshops & Night Market
Sunday at 10:00 AM
Chicago · Sanctuary Health
Winter Grower Workshop
Sat, Nov 7, 10:00 AM
Chicago · South Chicago Farm
Winter Grower Workshop
Sat, Nov 7, 10:00 AM
Chicago · South Chicago Farm
Sales end soon
Kinship Community Choir Big Sing
Sunday at 3:00 PM
Chicago · 2810 N Milwaukee Ave
Sales end soon
Kinship Community Choir Big Sing
Sunday at 3:00 PM
Chicago · 2810 N Milwaukee Ave
Best Price - Just Because 2026 Chicago Summer Holiday Bar Crawl
Sat, Jun 20, 4:00 PM
Chicago · Lincoln Park, River North, Wicker Park Bars All Access
Best Price - Just Because 2026 Chicago Summer Holiday Bar Crawl
Sat, Jun 20, 4:00 PM
Chicago · Lincoln Park, River North, Wicker Park Bars All Access
Going fast
Angel's Spring Fling Diva Drag Brunch
Saturday at 12:00 PM
North Riverside · Chef Shangri-La
Going fast
Angel's Spring Fling Diva Drag Brunch
Saturday at 12:00 PM
North Riverside · Chef Shangri-La
Almost full
Model Call #6 FINAL - FashionBar The Shows: April 2026
Sat, Mar 28, 12:00 PM
Chicago · Water Tower Place (Level 3)
Almost full
Model Call #6 FINAL - FashionBar The Shows: April 2026
Sat, Mar 28, 12:00 PM
Chicago · Water Tower Place (Level 3)
Third Coast Kettlebell x Chicago Strength
Sun, Apr 12, 11:00 AM
Chicago · Chicago Strength Logan Square
Third Coast Kettlebell x Chicago Strength
Sun, Apr 12, 11:00 AM
Chicago · Chicago Strength Logan Square
The Shops - Holiday Edition #1
Sat, Dec 12, 11:00 AM
Chicago · Water Tower Place (Level 3 Next to JJill and White House Black Market)
The Shops - Holiday Edition #1
Sat, Dec 12, 11:00 AM
Chicago · Water Tower Place (Level 3 Next to JJill and White House Black Market)
Limited Tickets - 2027 Chicago Winter Whiskey Tasting Festival (January 23)
Sat, Jan 23, 2:30 PM
Chicago · King's
Limited Tickets - 2027 Chicago Winter Whiskey Tasting Festival (January 23)
Sat, Jan 23, 2:30 PM
Chicago · King's

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