Drawing-painting Events in Chicago

Check out happening drawing-painting events all around Chicago, IL

Art Battle Chicago - January 23, 2026

 Fri, 23 Jan at 07:00 pm SPIN Chicago USD 20 to 29

Paint & Sip Brunch | Color Me Calm

 Sat, 14 Feb at 12:00 pm Chicago Sip & Paint USD 72 to 79

Holiday Brunch with Santa Benny

 Sun, 21 Dec at 09:00 am 1015 N Rush St., Chicago, IL

Sip & Paint Night Event Wednesdays 7:00 p.m. @ Tapster Lincoln Park

 Wed, 14 Jan at 07:00 pm Tapster Lincoln Park USD 39

“Hummingbirds” Paint Night Event Thursday 7:00 p.m. at Timeout Market

 Thu, 29 Jan at 07:00 pm TimeOut Market Chicago USD 39

“Hearts-Entwined” Paint Night Event Thursday 7:00 p.m. at Timeout Market

 Thu, 05 Feb at 07:00 pm TimeOut Market Chicago USD 39

BYOB Sip & Paint Class “Winter Wonderland”

 Fri, 26 Dec at 07:00 pm Sip & Paint USD 43

“ Vibrant-Sunset” Paint Night Event Thursday 7:00 p.m. at Timeout Market

 Thu, 22 Jan at 07:00 pm TimeOut Market Chicago USD 39

BYOB Sip & Paint Event - "Golden Forest"

 Sun, 21 Dec at 02:00 pm Chicago Sip & Paint USD 43

“ Venice Sunset” Sip and Paint Saturdays at 12:00 p.m. at Timeout Market

 Sat, 17 Jan at 12:00 pm TimeOut Market Chicago USD 39

Pink Christmas Sip and Paint

 Sun, 21 Dec at 06:00 pm Pink Flores Bakery & Cafe USD 51

“Borealis Nights” Paint Night Event Thursday 7:00 p.m. at Timeout Market

 Thu, 08 Jan at 07:00 pm TimeOut Market Chicago USD 39

“ Venice Sunset” Paint Night Event Thursday 7:00 p.m. at Timeout Market

 Thu, 15 Jan at 07:00 pm TimeOut Market Chicago USD 39

Romancing the Studio - A date night at the Gallery

 Fri, 13 Feb at 06:00 pm 5504 West Lawrence Avenue, Chicago, IL, USA USD 18

Sunday Funday Art Day

 Sun, 07 Dec at 10:00 am 5420 W Belmont Ave USD 8 to 43

December Sip and Paint

 Sat, 27 Dec at 05:00 pm 2842 W Chicago Ave USD 39 to 109

Paint Party!

 Fri, 09 Jan at 06:00 pm 2914 N Elston Ave, Chicago, IL, United States, Illinois 60618

Sip & Paint Night Event Wednesdays 7:00 p.m. @ Tapster Lincoln Park

 Wed, 07 Jan at 07:00 pm Tapster Lincoln Park USD 39

The Buttercream Canvas Series

 Fri, 13 Feb at 05:00 pm 1142 W 18th St USD 130 to 258

Winter Wonderland - A Sip and Paint at Eris Brewery and Cider House

 Wed, 21 Jan at 06:30 pm ERIS Brewery and Cider House USD 31

Life Drawing with Siren Betty Design and Roca - January 22, 2026

 Thu, 22 Jan at 06:00 pm Roca Chicago Downtown Showroom Free

FREE - New Year's Goal Collage Workshop

 Sun, 04 Jan at 03:00 pm Hey, I Thought Of You Free

Smooth Jazz Paint & Sip

 Wed, 14 Jan at 05:00 pm Privilege Restaurant Bar USD 34

Winter E-tegami Workshop at Gaijin

 Sat, 17 Jan at 03:00 pm Gaijin USD 34

Sip & Paint Night Event Wednesdays 7:00 p.m. @ Tapster Lincoln Park

 Wed, 21 Jan at 07:00 pm Tapster Lincoln Park USD 39

Sip & Paint Night Event Wednesdays 7:00 p.m. @ Tapster Lincoln Park

 Wed, 28 Jan at 07:00 pm Tapster Lincoln Park USD 39

Love Sip & Paint Night Event Wednesdays 7:00 p.m. @ Tapster Lincoln Park

 Wed, 11 Feb at 07:00 pm Tapster Lincoln Park USD 39

Crafts + Coffee

 Sat, 10 Jan at 01:00 pm Lot'sa USD 13 to 23

TAKEOVER TUESDAYS SIP & PAINT PARTY

 Tue, 11 Nov at 07:00 pm 8022 S Cottage Grove Ave Free

In Person Paint Night Event Wednesday 7:00 p.m. @ Tapster

 Wed, 19 Nov at 07:00 pm Tapster Lincoln Park USD 39

Wednesday Figure Drawing Session with Live Model

 Wed, 28 May at 06:00 pm 1579 N Milwaukee Ave suite 206 USD 45 to 174

DIY Stamp Carving

 Tue, 08 Jul at 05:00 pm 5420 W Belmont Ave USD 23

Floral Watercolor Workshop

 Tue, 26 Aug at 02:00 pm 5420 W Belmont Ave USD 23

Painting Pottery

 Thu, 02 Oct at 12:00 pm 5127 N Clark St USD 30

Dirty 30 Thursday's

 Thu, 27 Jun at 06:30 pm Creative Sippin USD 30