Drawing-painting Events in Chicago

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

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Fri, 16 Jan at 06:00 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Mon, 12 Jan at 08:30 pm Studio W.I.P. USD 62

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sun, 11 Jan at 01:00 pm Studio W.I.P. USD 62

Monet's Chicago Twilight - Paint and Sip in Chicago | Classpop!™

 Sat, 17 Jan at 07:30 pm Pinot's Palette - Logan Square USD 56

Paint Night Done Right - Chicago - Paint and Sip in Chicago | Classpop!™

 Sat, 24 Jan at 03:00 pm Wolf Point Distilling USD 55

Gold Coast Art Fair (68th annual)

 Sat, 20 Jun at 10:00 am Grant Park

Manet's Lilacs in a Vase - Paint and Sip in Chicago | Classpop!™

 Sat, 07 Feb at 03:00 pm Pinot's Palette - Logan Square USD 56

Glowing Starry Night - Chicago - Paint and Sip in Chicago | Classpop!™

 Sat, 14 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

Love Bandit - Paint and Sip in Chicago | Classpop!™

 Sat, 14 Feb at 12:00 pm Pinot's Palette - Logan Square USD 56

Psychedelic Paradise - Paint and Sip in Chicago | Classpop!™

 Fri, 06 Feb at 08:00 pm Pinot's Palette - Logan Square USD 56

Evergreen Moon - Paint and Sip in Chicago | Classpop!™

 Fri, 16 Jan at 08:00 pm Pinot's Palette - Logan Square USD 56

Van Gogh's Daisies and Poppies - Paint and Sip in Chicago | Classpop!™

 Sun, 11 Jan at 01:00 pm Pinot's Palette - Logan Square USD 56

Wino Sasquatch - Paint and Sip in Chicago | Classpop!™

 Thu, 15 Jan at 07:30 pm Pinot's Palette - Logan Square USD 49

Three Sunflowers - Paint and Sip in Chicago | Classpop!™

 Wed, 14 Jan at 07:30 pm Pinot's Palette - Logan Square USD 49

Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™

 Sat, 10 Jan at 03:30 pm Pinot's Palette - Logan Square USD 56

Aurora Reflections - Paint and Sip in Chicago | Classpop!™

 Sun, 11 Jan at 05:00 pm Pinot's Palette - Logan Square USD 56

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Thu, 15 Jan at 06:00 pm Studio W.I.P. USD 62

Lovely Hydrangeas - Paint and Sip in Chicago | Classpop!™

 Sat, 17 Jan at 03:30 pm Pinot's Palette - Logan Square USD 56

Sweet Succulents - Paint and Sip in Chicago | Classpop!™

 Sun, 18 Jan at 01:00 pm Pinot's Palette - Logan Square USD 56

Monet’s Water Lilies II - Paint and Sip in Chicago | Classpop!™

 Wed, 25 Feb at 07:00 pm Pinot's Palette - Logan Square USD 49

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Mon, 19 Jan at 06:00 pm Studio W.I.P. USD 62

Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™

 Wed, 21 Jan at 07:00 pm Pinot's Palette - Logan Square USD 32

Serene Moonlight - Paint and Sip in Chicago | Classpop!™

 Thu, 22 Jan at 07:00 pm Pinot's Palette - Logan Square USD 49

Moonlit Cherry Blossom River - Paint and Sip in Chicago | Classpop!™

 Thu, 22 Jan at 07:30 pm Pinot's Palette - Logan Square USD 49

Winter's Dream - Paint and Sip in Chicago | Classpop!™

 Fri, 23 Jan at 08:00 pm Pinot's Palette - Logan Square USD 56

Starry Night - Paint and Sip in Chicago | Classpop!™

 Sat, 24 Jan at 03:00 pm Ipsento 606 USD 55

Van Gogh's Blue Irises - Paint and Sip in Chicago | Classpop!™

 Sat, 24 Jan at 03:30 pm Pinot's Palette - Logan Square USD 56

Eventide - Paint and Sip in Chicago | Classpop!™

 Sat, 24 Jan at 07:30 pm Pinot's Palette - Logan Square USD 56

Moon Over the Pines - Paint and Sip in Chicago | Classpop!™

 Sun, 25 Jan at 05:00 pm Pinot's Palette - Logan Square USD 56

Van Gogh's Gladioli - Paint and Sip in Chicago | Classpop!™

 Sun, 25 Jan at 01:00 pm Pinot's Palette - Logan Square USD 56

Blowing Wishes - Paint and Sip in Chicago | Classpop!™

 Wed, 28 Jan at 07:00 pm Pinot's Palette - Logan Square USD 49

Wild Wander - Paint and Sip in Chicago | Classpop!™

 Thu, 29 Jan at 07:00 pm Pinot's Palette - Logan Square USD 49

Wildflowers at Paradise - Paint and Sip in Chicago | Classpop!™

 Thu, 29 Jan at 07:30 pm Pinot's Palette - Logan Square USD 49

A Moment of Peace - Paint and Sip in Chicago | Classpop!™

 Fri, 30 Jan at 07:30 pm Pinot's Palette - Logan Square USD 56

Galaxy Lake - Paint and Sip in Chicago | Classpop!™

 Sat, 31 Jan at 07:30 pm Pinot's Palette - Logan Square USD 56

Blossom Tree - Paint and Sip in Chicago | Classpop!™

 Sat, 31 Jan at 03:30 pm Pinot's Palette - Logan Square USD 56

Winter Sunset - Paint and Sip in Chicago | Classpop!™

 Thu, 05 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Waterfall Beach - Paint and Sip in Chicago | Classpop!™

 Wed, 04 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Misty Woodlands - Paint and Sip in Chicago | Classpop!™

 Sat, 07 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

Celestial Evening - Paint and Sip in Chicago | Classpop!™

 Sun, 08 Feb at 05:00 pm Pinot's Palette - Logan Square USD 56

Twilight Sorbet - Paint and Sip in Chicago | Classpop!™

 Sun, 08 Feb at 01:00 pm Pinot's Palette - Logan Square USD 56

Sweetheart Gnome - Paint and Sip in Chicago | Classpop!™

 Wed, 11 Feb at 07:00 pm Pinot's Palette - Logan Square USD 56

Psychedelic Starry Night - Paint and Sip in Chicago | Classpop!™

 Thu, 12 Feb at 07:00 pm Pinot's Palette - Logan Square USD 56

Amore Borealis Date Night - Paint and Sip in Chicago | Classpop!™

 Fri, 13 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

Wild Flower Forest - Paint and Sip in Chicago | Classpop!™

 Fri, 13 Feb at 04:00 pm Pinot's Palette - Logan Square USD 56

Van Gogh's Blue Vase - Paint and Sip in Chicago | Classpop!™

 Fri, 13 Feb at 08:00 pm Pinot's Palette - Logan Square USD 56

Cubist Portrait - Paint and Sip in Chicago | Classpop!™

 Sat, 14 Feb at 03:30 pm Pinot's Palette - Logan Square USD 56

River to My Heart (Date Night) - Paint and Sip in Chicago | Classpop!™

 Sun, 15 Feb at 06:00 pm Pinot's Palette - Logan Square USD 56

Japanese Crimson Moon - Paint and Sip in Chicago | Classpop!™

 Sun, 01 Feb at 05:00 pm Pinot's Palette - Logan Square USD 56

Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™

 Wed, 18 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Serene Sunrise - Paint and Sip in Chicago | Classpop!™

 Sun, 22 Feb at 01:00 pm Pinot's Palette - Logan Square USD 56

Forest at Twilight - Paint and Sip in Chicago | Classpop!™

 Sun, 22 Feb at 05:00 pm Pinot's Palette - Logan Square USD 56

Art Battle Chicago - January 23, 2026

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

Ghostly Gardens - Paint and Sip in Chicago | Classpop!™

 Wed, 25 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Galaxy Glow - Paint and Sip in Chicago | Classpop!™

 Thu, 26 Feb at 07:30 pm Pinot's Palette - Logan Square USD 49

Monet's Sunflowers - Paint and Sip in Chicago | Classpop!™

 Sat, 28 Feb at 03:00 pm Pinot's Palette - Logan Square USD 56

Midnight Glow - Paint and Sip in Chicago | Classpop!™

 Sat, 28 Feb at 07:30 pm Pinot's Palette - Logan Square USD 56

Sunday Funday Art Day

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

Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™

 Sat, 14 Feb at 04:00 pm Pinot's Palette - Logan Square USD 56

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

Build Your Pet Portrait: Acrylic Painting Workshop

 Sat, 24 Jan at 06:00 pm 5420 W Belmont Ave USD 31 to 37

“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

R&B Night Paint & Sip

 Sat, 31 Jan at 07:30 pm Lux Accents Studios USD 60 to 90

Paint & Sip Brunch | Color Me Calm

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

Monarchs for Migrants Art Fundraiser

 Fri, 30 Jan at 07:00 pm 5420 W Belmont Ave USD 49 to 61

Date Night Photography Class - Chicago - Photography Class by Classpop!™

 Sun, 11 Jan at 02:00 pm Digital Photo Academy Chicago USD 426

Teen Paint & Glow Event

 Sat, 31 Jan at 12:00 pm The Powerhouse Chicago Free

GLOW THEORY: Neon Paint & Sip

 Thu, 22 Jan at 07:00 pm RISE Dispensary at Salt Shed Chicago USD 21 to 39

“ 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

Sip and Paint-January 24

 Sat, 24 Jan at 05:00 pm 2842 W Chicago Ave USD 39 to 109

GB Figure Drawing: Christina

 Wed, 14 Jan at 07:00 pm 4201 N Ravenswood Ave, Chicago, IL 60613

“ 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

Paint and Sip Drinkware Session - Paint and Sip in Chicago | Classpop!™

 Tue, 13 Jan at 06:00 pm KaLab USD 40

Bieber Fever Themed Sip and Paint

 Fri, 16 Jan at 07:00 pm Mirella’s Tavern USD 36

Paint and Sip Drinkware Session - Paint and Sip in Chicago | Classpop!™

 Tue, 20 Jan at 06:00 pm KaLab USD 40

Sip and Paint -January 31

 Sat, 31 Jan at 05:00 pm 2842 W Chicago Ave USD 39 to 109

Snoopy Sip and Paint in Chicago

 Fri, 23 Jan at 07:00 pm Mirella’s Tavern USD 36

BYOB Sip & Paint Class “Starry Night Skyline”

 Sun, 11 Jan at 07:00 pm Sip & Paint USD 43

Paint Your Own Soup Crock @ Hotel Chocolat

 Wed, 21 Jan at 06:00 pm Hotel Chocolat USD 28

“ 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

Paint and Sip Drinkware Session - Paint and Sip in Chicago | Classpop!™

 Tue, 27 Jan at 06:00 pm KaLab USD 40

Family Paint Party Ages 5+ at BrentArt

 Sat, 24 Jan at 11:30 am BrentArt USD 37 to 67

BYOB Sip & Paint Class “Full Moon Magic”

 Sun, 11 Jan at 02:00 pm Sip & Paint USD 39

Snoopy Sip and Paint in Chicago

 Tue, 20 Jan at 07:00 pm La Licor Panamericana USD 36

GB Figure Drawing: Adelaide Nicolette

 Wed, 21 Jan at 07:00 pm 4201 N Ravenswood Ave, Chicago, IL 60613

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

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

Smooth Jazz Paint & Sip

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

The Buttercream Canvas Series

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

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

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

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

Winter E-tegami Workshop at Gaijin

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

Tarot Ceramic Tile Painting Workshop

 Wed, 21 Jan at 06:30 pm 1371 W Estes Ave USD 39

Let's Sketch the Auditorium Theatre

 Sun, 18 Jan at 12:00 pm Auditorium Theatre

Exploring Mixed Media Creativity: 1 Day Session in Chicago, IL

 Sat, 31 Jan at 09:00 am Regus - Chicago - 111 W. Jackson USD 551 to 716

Crafts + Coffee

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

Selena Paint Party

 Fri, 23 Jan at 07:00 pm 5420 W Belmont Ave USD 31