Ornament Paint & Sip Thu, 10 Dec at 06:30 pm Cafe Con Leche, North Milwaukee Avenue, Chicago, IL, USA USD 45 ART
Before Midnight - A Cinderella Tea Experience at The Ritz-Carlton, Chicago Sat, 19 Sep The Ritz-Carlton, Chicago FREE
Godfrey Wine Fest - Wine Tasting at I|O Godfrey Rooftop in Chicago Sat, 14 Nov at 01:00 pm IO Godfrey Rooftop Lounge USD 25 TO 42 FITNESS
Romansia: A La Orient Romantic Dinner & Show Sun, 13 Sep at 06:00 pm Alhambra Palace Restaurant USD 77 FITNESS
Chicago Exotic Paintings BYOB Wine and Paint Male Model Fri, 10 Mar at 09:00 pm 5425 W Lawrence Ave USD 44 ART
Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™ Sat, 21 Nov at 03:30 pm Pinot's Palette - Logan Square USD 56 ART
Grapes that crossed oceans: wine tasting journey & class Fri, 20 Nov at 06:00 pm Chicago Grand Gallery USD 68 TO 104 FITNESS
Birch Grove at Sunset - Paint and Sip in Chicago | Classpop!™ Sat, 14 Nov at 03:30 pm Pinot's Palette - Logan Square USD 56 FITNESS
Harry Potter Movies Trivia Night - Snakes & Lattes Chicago Tue, 17 Nov at 07:00 pm Snakes & Lattes Chicago USD 14 TO 74 ENTERTAINMENT
JEOPARDY! Bar League - Snakes & Lattes Chicago (US) Mon, 16 Nov at 07:00 pm Snakes & Lattes Chicago FREE FITNESS
GREEN WEDNESDAY at Spark’d South Loop! Wed, 25 Nov at 04:00 pm Spark'd Dispensary - South Loop FREE FITNESS
Chicago Exotic Paintings BYOB Wine & Paint Male Models Fri, 29 Jul at 07:00 pm 5425 W Lawrence Ave USD 44 FITNESS
TrapxCanvas - Chicago Sat, 14 Nov at 07:00 pm The Congress Plaza Hotel & Convention Center USD 44 FITNESS
Chicago Wine Fest at Hubbard Inn - Tastings Included Sat, 26 Dec at 05:00 pm Hubbard Inn USD 25 TO 42 FITNESS
Gingerbread House Build 2026 (by Habitat Chicago Associate Board) Sun, 06 Dec at 12:30 pm Pompei Restaurant USD 0 TO 50 FITNESS
"Sip, Paint, Give" at Midwest Coast Brewing Co. Wed, 18 Nov at 06:00 pm Midwest Coast Brewing Company USD 54 ART
Sip & Sculpt Pottery Workshop Thu, 17 Dec at 07:00 pm Pilot Project Brewing - Wrigleyville USD 82 FITNESS
Golden Hour Featuring Waack Attack Chicago Sat, 14 Nov at 05:00 pm Epiphany Center for the Arts FREE FITNESS
Couples Chocolate & Wine Tasting +Candle Making Experience Sat, 07 Feb at 05:00 pm Above Average DIY Candle Studio USD 97 WORKSHOPS
The Parlor Pour | A Curated Wine Dinner | Winter Menu Pairing Thu, 10 Dec at 06:30 pm Colvin House USD 130 FITNESS
R&B Night Paint & Sip: Autumn in a Glass Sat, 14 Nov at 07:30 pm Lux Accents Studios USD 80 TO 145 FITNESS
A Toast to Gratitude Featuring Moët & Chandon Sat, 21 Nov at 08:00 pm Ambassador Gold Coast - The Chicago Hotel Collection USD 34 TO 66 FITNESS
Giving Thanks - Why Bread? Why Wine? Thu, 19 Nov at 06:15 pm 1711 N Cleveland Ave room 110 FREE FITNESS
Ballroom Class For Couples (West Loop) Wed, 27 May at 07:30 pm Ballroom Dance Chicago Loft USD 87 FITNESS
Intro to Argentine Tango Class For Couples Wed, 27 May at 06:45 pm Ballroom Dance Chicago USD 87 WORKSHOPS
Beginner Friendly Chunky Hand Knitting Workshop Mon, 25 May at 12:00 pm 3414 W Foster Ave USD 75 WORKSHOPS
AGBU YP Chicago Kickoff! Fri, 20 Nov at 06:00 pm The Honorary Consulate of the Republic of Armenia in Chicago FOOD-DRINKS
Love After Dark - Sensual Couples Candle Making Experience Fri, 24 Oct at 09:00 pm 3414 W Foster Ave USD 107 FITNESS
Got Glögg? Fri, 20 Nov at 07:00 pm 5211 N Clark St, Chicago, IL, United States, Illinois 60640 CONTESTS
Grab the Gals for our Autumn Boots Sip and Paint Sat, 21 Nov at 07:00 pm Toast To Paint USD 35 TO 46 FITNESS
End of Season Dinner at Chicago Chophouse: Prime Rib Buffet & Drinks Fri, 11 Dec at 06:00 pm Chicago Chop House USD 80 FOOD-DRINKS
Wine & Waisted: An Intimate Waist Beads Experience Sat, 14 Nov at 07:00 pm U-Haul Artist Lofts USD 32 FITNESS
MATTER Holiday Happy Hour Thu, 03 Dec at 04:00 pm 222 W Merchandise Mart Plaza, Suite 228 FREE FITNESS
Opening of the Westside Darkroom & The Darkroom Chicago’s 2nd Anniversary Sat, 14 Nov at 11:00 am Theatre Y USD 0 TO 10,673 FITNESS
Chicago-Style Executive Dinner at Unico Restaurante 12/2 Wed, 02 Dec at 06:00 pm Unico Restaurante USD 104 FITNESS
WINE SEMINAR Wed, 09 Dec at 07:00 pm Kennedy Rooftop / Hyatt Place Chicago Wicker Park USD 45 FITNESS